Substituted 4-benzoylpyrazoles

ABSTRACT

4-Benzoylpyrazoles of the formula I ##STR1## useful for controlling harmful plants, are disclosed.

This application is a 371 of PCT/EP98/04481 filed Jul. 20, 1998.

The present invention relates to substituted 4-benzoylpyrazoles of the formula I ##STR2## where: R¹ and R² are each hydrogen, mercapto, nitro, halogen, cyano, thiocyanato, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy, C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, --OR³, --OCOR³, --OSO₂ R³, --S(O)_(n) R³, --SO₂ OR³, --SO₂ N(R³)₂, --NR³ SO₂ R³ or --NR³ COR³ ;

R³ is hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, phenyl or phenyl-C₁ -C₆ -alkyl; where the alkyl radicals mentioned may be partially or fully halogenated and/or carry one to three of the following groups:

hydroxyl, mercapto, amino, cyano, R³, --OR³, --SR³, --N(R³)₂, ═NOR³, --OCOR³, --SCOR³, --NR³ COR³, --CO₂ R³, --COSR³, --CON(R³)₂, C₁ -C₄ -alkyliminooxy, C₁ -C₄ -alkoxyamino, C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkoxy-C₂ -C₆ -alkoxycarbonyl, C₁ -C₄ -alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the eight last-mentioned radicals may in turn be substituted;

n is 0, 1 or 2;

Q is a pyrazole of the formula II which is attached in position 4, ##STR3## where R⁴ is hydrogen, C₁ -C₆ -alkyl or C₁ -C₆ -haloalkyl;

R⁵ is C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, phenyl or phenyl which may be partially or fully halogenated and/or carry one to three of the following radicals:

nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy;

R⁶ is hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkylcarbonyl, C₁ -C₆ -haloalkylcarbonyl, C₁ -C₆ -alkoxycarbonyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆ -haloalkylsulfonyl, phenylcarbonyl, phenylcarbonylmethyl, phenoxycarbonyl or phenylsulfonyl,

where the four last-mentioned substituents are either unsubstituted, or the phenyl ring may in each case be partially or fully halogenated and/or carry one to three of the following radicals:

nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy;

X¹ is a straight-chain or branched C₁ -C₆ -alkylene, a C₂ -C₆ -alkenylene or a C₂ -C₆ -alkynylene chain, where the alkylene, alkenylene or alkynylene radicals mentioned may be partially halogenated and/or carry one to three of the following groups:

--OR⁷, --OCOR⁷, --OCONHR⁷ or --OSO₂ R⁷,

and where those of the alkenylene radicals mentioned are excluded where the double bond is α,β to the phenyl ring and where Het is linked to the double bond via the β position;

R⁷ is hydrogen, C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, phenyl, phenyl-C₁ -C₆ -alkyl, where the alkyl, alkenyl or alkynyl radicals mentioned may be partially or fully halogenated and/or substituted by one or more of the following radicals:

hydroxyl, mercapto, amino, cyano, nitro, formyl, C₁ -C₄ -alkylamino, C₁ -C₄ -dialkylamino, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkylcarbonyloxy, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy;

Het is a three- to six-membered, partially or fully saturated heterocyclic group or a three- to six-membered heteroaromatic group having up to three hetero atoms selected from the group consisting of:

nitrogen, oxygen or sulfur,

where the heterocyclic or heteroaromatic group mentioned may be partially or fully halogenated and/or substituted by R⁸ ;

R⁸ is hydrogen, hydroxyl, mercapto, amino, cyano, nitro, formyl, C₁ -C₄ -alkylamino, C₁ -C₄ -dialkylamino, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkylcarbonyloxy, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, where in all instances each of the alkyl radicals may be substituted by one or more of the following radicals:

cyano, formyl, C₁ -C₄ -alkylamino, C₁ -C₄ -dialkylamino, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkylcarbonyloxy, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy;

and agriculturally useful salts thereof.

Moreover, the invention relates to processes and intermediates for preparing compounds of the formula I, to compositions comprising them and to the use of the compounds of the formula I and of compositions comprising them for controlling harmful plants.

The literature, for example EP-A 282 944, discloses 4-benzoylpyrazoles.

However, the herbicidal properties of the prior art compounds and their crop safety are not entirely satisfactory.

It is an object of the present invention to provide novel, in particular herbicidally active, compounds having improved properties.

We have found that this object is achieved by the 4-benzoylpyrazoles of the formula I according to the invention and their herbicidal activity.

Furthermore, we have found herbicidal compositions which comprise the compounds I and have very good herbicidal activity. Additionally, we have found processes for preparing these compositions and methods for controlling undesirable vegetation using the compounds I.

The present invention also provides stereoisomers of the compounds of the formula I. Both pure stereoisomers and mixtures are included.

Depending on the substitution pattern, the compounds of the formula I may contain one or more chiral centers, in which case they exist in the form of enantiomers or diastereomer mixtures. The invention provides both the pure enantiomers or diastereomers and mixtures thereof.

The compounds of the formula I may also be present in the form of their agriculturally useful salts, the kind of salt generally not being important. The salts of those cations or the acid addition salts of those acids whose cations or anions, respectively, do not adversely affect the herbicidal activity of the compounds I are generally suitable.

Suitable cations are in particular ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and ammonium where, if desired, one to four hydrogen atoms may be replaced by C₁ -C₄ -alkyl or hydroxy-C₁ -C₄ -alkyl and/or one phenyl or benzyl, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C₁ -C₄ -alkyl)sulfonium, and sulfoxonium ions, preferably tri(C₁ -C₄ -alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C₁ -C₄ -alkanoic acids, preferably formate, acetate, propionate and butyrate.

Process A

Reactions of pyrazoles of the formula II (where R⁶ =H) with an activated carboxylic acid IIIa or a carboxylic acid IIIb, which is preferably activated in situ, to give the acylation product V, and subsequent rearrangement to the compounds of the formula I according to the invention. ##STR4##

L¹ is a nucleophilically replaceable leaving group such as halogen, for example bromine or chlorine, hetaryl, for example imidazolyl or pyridyl, or carboxylate, for example acetate, trifluoroacetate, etc.

The activated carboxylic acid can be employed directly, as in the case of the acyl halides, or be generated in situ, for example by using dicyclohexylcarbodiimide, triphenylphosphine/azodicarboxylic esters, 2-pyridine disulfite/triphenylphosphine, carbonyldiimidazole, etc.

It may be advantageous to carry out the acylation reaction in the presence of a base. Starting materials and auxiliary base are advantageously employed in equimolar amounts. A slight excess of auxiliary base, for example 1.2 to 1.5 mol equivalents, based on II, may be advantageous under certain circumstances.

Suitable auxiliary bases are tertiary alkylamines, pyridine or alkali metal carbonates. Examples of solvents which can be used are chlorinated hydrocarbons, such as methylene chloride, 1,2-dichloroethane, aromatic hydrocarbons, such as toluene, xylene, chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide, dimethyl sulfoxide, or esters such as ethyl acetate or mixtures of these.

If acyl halides are employed as activated carboxylic acid component, it may be advantageous to cool the reaction mixture to 0-10° C. when adding this reaction partner. The mixture is subsequently stirred at 20-100° C., preferably at 25-50° C., until the reaction is complete. Work-up is carried out in the customary manner, for example by pouring the reaction mixture into water and extracting the product of value. Solvents which are particularly suitable for this purpose are methylene chloride, diethyl ether and ethyl acetate. After the organic phase has been dried and the solvent has been removed, the crude enol ester of the formula V is purified, preferably by chromatography. Alternatively, it is possible to employ the crude enol ester of the formula V without further purification for the rearrangement reaction.

The rearrangement of the enol esters of the formula V to the compounds of the formula I is advantageously carried out at from 20 to 40° C. in a solvent and in the presence of a base and, if appropriate, in the presence of a cyano compound.

Examples of solvents which can be used are acetonitrile, methylene chloride, 1,2-dichloroethane, dioxane, ethyl acetate, toluene or mixtures of these. Preferred solvents are acetonitrile and dioxane.

Suitable bases are tertiary amines such as triethylamine, pyridine or alkali metal carbonates, such as sodium carbonate, potassium carbonate, which are preferably employed in equimolar amounts or up to a four-fold excess, based on the ester.

Preference is given to using triethylamine or alkali metal carbonates.

Suitable cyano compounds are inorganic cyanides such as sodium cyanide, potassium cyanide and organic cyano compounds such as acetone cyanohydrin, trimethylsilyl cyanide. They are employed in an amount of 1 to 50 mol percent, based on the ester. Preference is given to using acetone cyanohydrin or trimethylsilyl cyanide, for example, in an amount of 5 to 15, preferably 10, mol percent, based on the ester.

Particular preference is given to employing alkali metal carbonates, such as potassium carbonate, in acetonitrile or dioxane.

Work-up can be carried out in a manner known per se. For example, the reaction mixture is acidified with dilute mineral acid, such as 5% strength hydrochloric acid or sulfuric acid, and extracted with an organic solvent, for example methylene chloride, ethyl acetate. The organic phase can be extracted with 5-10% strength alkali metal carbonate solution, for example sodium carbonate or potassium carbonate solution. The aqueous phase is acidified, and the precipitate which forms is filtered off with suction and/or extracted with methylene chloride or ethyl acetate, dried and concentrated.

(Examples of the synthesis of esters from hydroxypyrazoles and the rearrangement of the esters are mentioned, for example, in EP-A 282 944 or U.S. Pat. No. 4,643,757).

Process B

Reactions of 4-benzoylpyrazoles of the formula I (where R⁶ =H) with a compound of the formula IV (where R⁶ ≠H): ##STR5##

L² is a nucleophilically replaceable leaving group such as halogen, for example bromine, chlorine, hetaryl, for example imidazolyl, pyridyl, carboxylate, for example acetate, trifluoroacetate, sulfonate, for example mesylate, triflate, etc.

The compounds of the formula IV can be employed directly, for example in the case of the alkyl halides, acyl halides, sulfonyl halides, carboxylic anhydrides and sulfonic anhydrides, or prepared in situ, for example activated carboxylic acids (by means of carboxylic acid and dicyclohexylcarbodiimide, carbonyldiimidazole, etc.).

In general, the starting materials are employed in an equimolar ratio. However, it may also be advantageous to employ an excess of one or the other component.

Where appropriate, it may be advantageous to carry out the reaction in the presence of a base. The starting materials and the auxiliary base are advantageously employed in equimolar amounts. Under certain circumstances, it may be advantageous to employ an excess of the auxiliary base, for example 1.5 to 3 mol equivalents, based on Ia.

Suitable auxiliary bases are tertiary alkylamines such as triethylamine, pyridine, alkali metal carbonates, for example sodium carbonate, potassium carbonate, and alkali metal hydrides, for example sodium hydride. Preference is given to using triethylamine, pyridine and potassium carbonate.

Examples of suitable solvents are chlorinated hydrocarbons such as methylene chloride, 1,2-dichloroethane, aromatic hydrocarbons, for example toluene, xylene, chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide, dimethyl sulfoxide or esters, such as ethyl acetate, or mixtures of these.

The reaction temperature is generally in the range of from 0° C. to the boiling point of the reaction mixture.

Work-up can be carried out in a manner known per se.

The benzoic acids of the formula III are novel, ##STR6## the variables being defined as follows: R¹ and R² are each hydrogen, mercapto, nitro, halogen, cyano, thiocyanato, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy, C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, --OR³, --OCOR³, --OSO₂ R³, --S(O)_(n) R³, --SO₂ OR³, --SO₂ N(R³)₂, --NR³ SO₂ R³ or --NR³ COR³ ;

R³ is hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, phenyl or phenyl-C₁ -C₆ -alkyl; where the alkyl radicals mentioned may be partially or fully halogenated and/or carry one to three of the following groups:

hydroxyl, mercapto, amino, cyano, R³, --OR³, --SR³, --N(R³)₂, ═NOR³, --OCOR³, --SCOR³, --NR³ COR³, --CO₂ R³, --COSR³, --CON(R³)₂, C₁ -C₄ -alkyliminooxy, C₁ -C₄ -alkoxyamino, C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkoxy-C₂ -C₆ -alkoxycarbonyl, C₁ -C₄ -alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the eight last-mentioned radicals may in turn be substituted;

n is 0, 1 or 2;

X¹ is a straight-chain or branched C₁ -C₆ -alkylene, a C₂ -C₆ -alkenylene or a C₂ -C₆ -alkynylene chain, where the alkyl, alkenyl or alkynyl radicals mentioned may be partially halogenated and/or carry one to three of the following groups:

--OR⁷, --OCOR⁷, --OCONHR⁷ or --OSO₂ R⁷,

and where those of the alkenylene radicals mentioned are excluded where the double bond is α,β to the phenyl ring and where Het is linked to the double bond via the β position.

R⁷ is hydrogen, C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, phenyl, phenyl-C₁ -C₆ -alkyl, where the alkyl, alkenyl or alkynyl radicals mentioned may be partially or fully halogenated and/or substituted by one or more of the following radicals:

hydroxyl, mercapto, amino, cyano, nitro, formyl, C₁ -C₄ -alkylamino, C₁ -C₄ -dialkylamino, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkylcarbonyloxy, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy;

Het is a three to six-membered, partially or fully saturated heterocyclic group or a three to six-membered heteroaromatic group having up to three hetero atoms selected from the group consisting of:

nitrogen, oxygen or sulfur,

where the heterocyclic or heteroaromatic group mentioned may be partially or fully halogenated and/or substituted by R⁸ ;

R⁸ is hydrogen, hydroxyl, mercapto, amino, cyano, nitro, formyl, C₁ -C₄ -alkylamino, C₁ -C₄ -dialkylamino, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkylcarbonyloxy, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, where in all instances each of the alkyl radicals may be substituted by one or more of the following radicals:

cyano, formyl, C₁ -C₄ -alkylamino, C₁ -C₄ -dialkylamino, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkylcarbonyloxy, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy;

R⁹ is hydroxyl or a hydrolyzable radical.

Examples of hydrolyzable radicals are alkoxy, phenoxy, alkylthio, phenylthio radicals with or without substitution, halides, hetaryl radicals which are attached via nitrogen, amino, imino radicals with or without substitution, etc.

Preference is given to benzoyl halides IIIa where L¹ =halogen (III where R⁹ =halogen), ##STR7## where the variables R¹, R², X¹ and Het are each as defined under formula III and

L¹ is halogen, in particular chlorine or bromine.

Likewise, preference is given to benzoic acids of the formula IIIb (III where R⁹ =hydroxyl), ##STR8## where the variables R¹, R², X¹ and Het are each as defined under formula III.

Likewise, preference is given to benzoic esters of the formula IIIc (III where R⁹ =C₁ -C₆ -alkoxy), ##STR9## where the variables R¹, R², X¹ and Het are each as defined under formula III and

M is C₁ -C₆ -alkoxy.

The compounds of the formula IIIa (where L¹ =halogen) can be prepared similarly to methods known from the literature (cf. L. G. Fieser, M. Fieser "Reagents for Organic Synthesis", Vol. I, p. 767-769 (1967)) by reacting benzoic acids of the formula IIIb with halogenating agents such as thionyl chloride, thionyl bromide, phosgene, diphosgene, triphosgene, oxalyl chloride, oxalyl bromide.

The benzoic acids of the formula IIIb can be obtained inter alia by hydrolysis of the benzoic esters of the formula IIIc (where M=C₁ -C₆ -alkoxy).

The benzoic esters of the formula IIIc according to the invention are preparable by various methods known from the literature (for example a. G. Dittus in Houben-Weyl, Methoden der Organischen Chemie, Volume VI/3, Sauerstoff-Verbindungen I, 4th edition, p. 493 ff., Georg Thieme Verlag, 1965; b. T. L. Gilchrist, Heterocyclenchemie, 2nd edition, Verlag Chemie, 1995), and illustrated in the examples below.

Process C

Metallation of suitable benzoic esters IIIc ortho to the ester function using strong, organometallic bases, and subsequent 1,2-addition of a carbonyl compound V affords the benzoic esters IIIe according to the invention, ##STR10## where R¹⁰ is a substituent R¹ suitable for ortho metallation (for example V. Snieckus, Chem. Rev., 1990, 90, 879), preferably halogen and C₁ -C₆ -alkoxy and

X² is a straight-chain or branched C₁ -C₅ -alkylene, a C₂ -C₅ -alkenylene or a C₂ -C₅ -alkynylene chain, where the alkylene, alkenylene or alkynylene radicals mentioned may be partially halogenated and/or carry one to three of the following groups:

--OR⁷, --OCOR⁷, --OCONHR⁷ or --OSO₂ R⁷.

Organometallic bases which are suitable for ortho-metallation of the benzoic esters IIId known from the literature are, for example, alkyllithium compounds, preferably n-butyllithium or sec-butyllithium, lithium dialkylamides, preferably lithium diisopropylamide or sodium hexamethyldisilazide.

Suitable inert solvents for the direct ortho-metallation are, for example, tetrahydrofuran, diethyl ether, 1,2-dimethoxyethane or 1,4-dioxane, dimethylformamide, dimethyl sulfoxide, methyl tert-butyl ether or else mixtures of these solvents.

The reaction temperatures may be from -80 to 100° C., preferably from -80 to 40° C.

The reaction of the ortho-metallated benzoic esters IIId, which are generated in situ, with the aldehydes V is carried out at from -80 to 100° C.

The products IIIe according to the invention contain a hydroxymethylene group which is suitable for further derivatizations by methods known from the literature. Thus, the hydroxymethylene group can, for example, be methylated to the methoxy group. ##STR11## Process D

1,3-dipolar cycloaddition of the benzoic esters IIIg with olefins or acetylenes with or without substitution under dehydrating conditions affords the benzoic esters according to the invention, for example IIIh. ##STR12##

The dehydration according to the method of Mukaiyama is preferably carried out using aromatic isocyanates (for example T. Mukaiyama et al., J. Am. Chem. Soc. 1960, 82, 5339), for example phenyl isocyanate or 4-chlorophenyl isocyanate.

In the variant according to Shimizu, aliphatic chloroformates (for example T. Shimizu et al., Bull. Chem. Soc. Jpn. 1986, 59, 2827), preferably ethyl chloroformate, can also be used.

More recent developments show that, for example, N,N-diethylaminosulfur trifluoride (DAST), (methoxycarbonylsulfamoyl)triethylammonium hydroxide (Burgess Reagent), phosphoryl chloride (for example C. Mioskowski et al., Tetrahedron Letters 1997, 38, 1547) or else a combination of di-tert-butyl dicarbonate (Boc₂ O) and 4-dimethylaminopyridine (DMAP) (A. Hassner et al., Synthesis 1997, 309) can likewise be employed successfully as dehydrating agents for the generation of nitrile oxides.

The nitrile oxides formed in this manner in situ can be reacted at from room temperature to the boiling point of the solvent used with any substituted olefins or acetylene to give the benzoic esters IIIc according to the invention, X¹ in this case being, for example, a methylene group and Het an isoxazole or isoxazoline skeleton with or without substitution.

The cycloaddition is carried out in inert solvents, for example toluene, chloroform or acetonitrile.

The benozoic ester IIIg can be obtained by reduction according to methods known from the literature from IIIj, which is preparable by nitroolefination (for example a. V. V. Perekalin et al., Nitroalkenes, John Wiley & Sons Ltd., New York 1994, b. A. G. M. Barrett et al., Chem. Rev. 1986, 86, 751) of the corresponding aldehyde IIIi. ##STR13##

Preference is given to compounds of the formula I according to the invention where the group X¹ is either a C₁ -C₂ -alkylene or a C₂ -alkenylene chain and

Het is a three- to six-membered, partially or fully saturated heterocyclic group or a three- to six-membered heteroaromatic group having up to three hetero atoms selected from the group consisting of:

nitrogen, oxygen and sulfur,

where the heterocyclic or heteroaromatic group mentioned may be partially or fully halogenated and/or may be substituted by R⁸.

In addition, preference is given to compounds of the formula I according to the invention where the group Het is a five- or six-membered, partially or fully saturated heterocyclic or a five- or six-membered heteroaromatic group having up to three hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, where the heterocyclic or heteroaromatic group mentioned may be partially or fully halogenated and/or substituted by R⁸ ;

R⁸ is hydrogen, hydroxyl, mercapto, amino, cyano, nitro, formyl, C₁ -C₄ -alkylamino, C₁ -C₄ -dialkylamino, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkylcarbonyloxy, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, where in all instances each of the alkyl radicals may be substituted by one or more of the following radicals:

cyano, formyl, C₁ -C₄ -alkylamino, C₁ -C₄ -dialkylamino, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkylcarbonyloxy, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy.

The organic moieties mentioned for the substituents R¹ -R¹⁰ or as radicals on phenyl, hetaryl and heterocyclyl rings are collective terms for individual enumerations of the individual group members. All hydrocarbon chains, ie. all alkyl, haloalkyl, cycloalkyl, alkoxyalkyl, alkoxy, haloalkoxy, alkyliminooxy, alkoxyamino, alkylsulfonyl, haloalkylsulfonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkoxyalkoxycarbonyl, alkenyl, cycloalkenyl, alkynyl moieties can be straight-chain or branched. Unless otherwise specified, halogenated substituents preferably have attached to them one to five identical or different halogen atoms, the meaning of halogen being in each case fluorine, chlorine, bromine or iodine.

Examples of other meanings are:

C₁ -C₄ -alkyl, and the alkyl moieties of C₁ -C₄ -alkylcarbonyl: methyl, ethyl, n-propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl;

C₁ -C₆ -alkyl and the alkyl moieties of C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl and C₁ -C₆ -alkylcarbonyl: C₁ -C₄ -alkyl as mentioned above, and also pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-3-methylpropyl;

C₁ -C₄ -haloalkyl: a C₁ -C₄ -alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, e.g. chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl and nonafluorobutyl;

C₁ -C₆ -haloalkyl and the haloalkyl moieties of C₁ -C₆ -haloalkylcarbonyl: C₁ -C₄ -haloalkyl as mentioned above, and also 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl and dodecafluorohexyl;

C₁ -C₄ -alkoxy and the alkoxy moieties of C₁ -C₄ -alkoxyamino, C₁ -C₄ -alkoxy-C₂ -C₆ -alkoxycarbonyl and C₁ -C₄ -alkoxycarbonyl: methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy;

C₁ -C₆ -alkoxy and the alkoxy moieties of C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy-C₂ -C₆ -alkyl, C₁ -C₄ -alkoxy-C₂ -C₆ -alkoxycarbonyl and C₁ -C₆ -alkoxycarbonyl: C₁ -C₄ -alkoxy as mentioned above, and also pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methoxylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy;

C₁ -C₄ -haloalkoxy: a C₁ -C₄ -alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, e.g. fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy and nonafluorobutoxy;

C₁ -C₄ -alkylsulfonyl (C₁ -C₄ -alkyl-S(═O)₂ --): methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl and 1,1-dimethylethylsulfonyl;

C₁ -C₆ -alkylsulfonyl: C₁ -C₄ -alkylsulfonyl as mentioned above, and also pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl;

C₁ -C₆ -haloalkylsulfonyl: a C₁ -C₆ -alkylsulfonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, ie. fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, pentafluoroethylsulfonyl, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl, 2,2,3,3,3-pentafluoropropylsulfonyl, heptafluoropropylsulfonyl, 1-(fluoromethyl)-2-fluoroethylsulfonyl, 1-(chloromethyl)-2-chloroethylsulfonyl, 1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl, nonafluorobutylsulfonyl, 5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-bromopentylsulfonyl, 5-iodopentylsulfonyl, 6-fluorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl and dodecafluorohexylsulfonyl;

C₁ -C₄ -alkyliminooxy: methyliminooxy, ethyliminooxy, 1-propyliminooxy, 2-propyliminooxy, 1-butyliminooxy and 2-butyliminooxy;

C₃ -C₆ -alkenyl: prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl, buten-1-yl, buten-2-yl, buten-3-yl, 1-methylprop-1-en-1-yl, 2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, penten-1-yl, penten-2-yl, penten-3-yl, penten-4-yl, 1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl, 3-methylbut-1-en-1-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-1-en-1-yl, 1,2-dimethylprop-2-en-1-yl, 1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-1-yl, hex-1-en-1-yl, hex-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl, 1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl, 1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl, 3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-1-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl, 2-ethylbut-1-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl, 1-ethyl-2-methylprop-1-en-1-yl and 1-ethyl-2-methylprop-2-en-1-yl; p1 C₂ -C₆ -alkenyl: C₃ -C₆ -alkenyl as mentioned above, and also ethenyl;

C₃ -C₆ -alkynyl: prop-1-yn-1-yl, prop-2-yn-1-yl, but-1-yn-1-yl, but-1-yn-3-yl, but-1-yn-4-yl, but-2-yn-1-yl, pent-1-yn-1-yl, pent-1-yn-3-yl, pent-1-yn-4-yl, pent-1-yn-5-yl, pent-2-yn-1-yl, pent-2-yn-4-yl, pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl, hex-1-yn-1-yl, hex-1-yn-3-yl, hex-1-yn-4-yl, hex-1-yn-5-yl, hex-1-yn-6-yl, hex-2-yn-1-yl, hex-2-yn-4-yl, hex-2-yn-5-yl, hex-2-yn-6-yl, hex-3-yn-1-yl, hex-3-yn-2-yl, 3-methylpent-1-yn-1-yl, 3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-1-yn-1-yl, 4-methylpent-2-yn-4-yl and 4-methylpent-2-yn-5-yl;

C₂ -C₆ -alkynyl: C₃ -C₆ -alkynyl as mentioned above, and also ethynyl:

C₃ -C₆ -cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

C₄ -C₆ -cycloalkenyl: cyclobuten-1-yl, cyclobuten-3-yl, cyclopenten-1-yl, cyclopenten-3-yl, cyclopenten-4-yl, cyclohexen-1-yl, cyclohexen-3-yl and cyclohexen-4-yl;

heterocyclyl, and also the heterocyclyl radicals in heterocyclyloxy: three- to seven-membered saturated or partially unsaturated mono- or polycyclic heterocycles which contain one to three hetero atoms selected from a group consisting of oxygen, nitrogen and sulfur, such as oxiranyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,3-dihydrofuran-4-yl, 2,3-dihydrofuran-5-yl, 2,5-dihydrofuran-2-yl, 2,5-dihydrofuran-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,3-dihydrothien-4-yl, 2,3-dihydrothien-5-yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 2,3-dihydropyrrol-2-yl, 2,3-dihydropyrrol-3-yl, 2,3-dihydropyrrol-4-yl, 2,3-dihydropyrrol-5-yl, 2,5-dihydropyrrol-2-yl, 2,5-dihydropyrrol-3-yl, 2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl, 2,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-4-yl, 2,5-dihydroxazol-5-yl, 2,3-dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-5-yl, 4,5-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl, 4,5-dihydroisothiazol-5-yl, 2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol -5-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,5-dihydropyrazol-3-yl, 2,5-dihydropyrazol-4-yl, 2,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 4,5-dihydrooxazol-2-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-2-yl, 2,5-dihydrooxazol-4-yl, 2,5-dihydrooxazol-5-yl, 2,3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 4,5-dihydrothiazol-2-yl, 4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl, 2,3-dihydroimidazol-2-yl, 2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5-yl, 4,5-dihydroimidazol-2-yl, 4,5-dihydroimidazol-4-yl, 4,5-dihydroimidazol-5-yl, 2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl, 2, 5-dihydroimidazol-5-yl, 2-morpholinyl, 3-morpholinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-tetrahydropyridazinyl, 4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl, 4-tetrahydropyrimidinyl, 5-tetrahydropyrimidinyl, 2-tetrahydropyrazinyl, 1,3,5-tetrahydrotriazin-2-yl, 1,2,4-tetrahydrotriazin-3-yl, 1,3-dihydrooxazin-2-yl, 1,3-dithian-2-yl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothiopyranyl, 3-tetrahydrothiopyranyl, 4-tetrahydrothiopyranyl, 1,3-dioxolan-2-yl, 3,4,5,6-tetrahydropyridin-2-yl, 4H-1,3-thiazin-2-yl, 4H-3,1-benzothiazin-2-yl, 1,1-dioxo-2,3,4,5-tetrahydrothien-2-yl, 2H-1,4-benzothiazin-3-yl, 2H-1,4-benzoxazin-3-yl, 1,3-dihydrooxazin-2-yl,

hetaryl, and also the hetaryl radicals in hetaryloxy:

aromatic mono- or polycyclic radicals which, besides carbon ring members, may additionally contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one sulfur atom, e.g. 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4,5-tetrazin-3-yl, and also the corresponding benzo-fuzed derivatives.

All phenyl, hetaryl and heterocyclyl rings are preferably unsubstituted or have attached to them one to three halogen atoms and/or one or two radicals selected from the following group: nitro, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy or methoxycarbonyl.

With a view to the use of the compounds of the formula I according to the invention as herbicides, the variables preferably have the following meanings, viz. in each case alone or in combination:

R¹ is nitro, halogen, cyano, thiocyanato, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, --OR³ or --S(O)_(n) R³ ;

particularly preferably nitro, halogen such as fluorine, chlorine or bromine, C₁ -C₆ -haloalkyl, --OR³ or --SO₂ R³ ;

R² is hydrogen, nitro, halogen, cyano, thiocyanato, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, --OR³ or --S(O)_(n) R³ ;

particularly preferably hydrogen, nitro, halogen such as fluorine, chlorine or bromine, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, --OR³ or --SO₂ R³ ;

R³ is hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, phenyl or phenyl-C₁ -C₆ -alkyl;

particularly preferably hydrogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₂ -C₃ -alkenyl, C₂ -C₃ -alkynyl or phenyl; where the alkyl radicals mentioned may be partially or fully halogenated and/or may carry one to three of the following groups:

hydroxyl, mercapto, amino, cyano, R³, --OR³, --SR³, --N(R³)₂, ═NOR³, --OCOR³, --SCOR³, --NR³ COR³, --CO₂ R³, --COSR³, --CON(R³)₂, C₁ -C₄ -alkyliminooxy, C₁ -C₄ -alkoxyamino, C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkoxy-C₂ -C₆ -alkoxycarbonyl, C₁ -C₄ -alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the eight last-mentioned radicals may in turn be substituted;

n is 0, 1 or 2, particularly preferably 0 or 2;

R⁴ is hydrogen, C₁ -C₆ -alkyl or C₁ -C₆ -haloalkyl; particularly preferably hydrogen, methyl, ethyl or trifluoromethyl;

R⁵ is C₁ -C₆ -alkyl or C₁ -C₆ -haloalkyl; particularly preferably methyl, ethyl, propyl, isopropyl, butyl or isobutyl;

R⁶ is hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -alkylcarbonyl, C₁ -C₆ -haloalkylcarbonyl, C₁ -C₆ -alkoxycarbonyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆ -haloalkylsulfonyl, phenylcarbonylmethyl or phenylsulfonyl, where the phenyl ring of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy;

X¹ is a straight-chain or branched C₁ -C₄ -alkylene, a propenylene or butenylene or a C₂ -C₄ -alkynylene chain, particularly preferably a methylene, ethylene, propylene, propenylene, ethynylene or propynylene chain, where the alkylene, alkenylene or alkynylene radicals mentioned may be partially halogenated and/or may carry one to three of the following groups:

--OR⁷, --OCOR⁷, --OCONHR⁷ or --OSO₂ R⁷,

and where those of the alkenylene radicals mentioned are excluded where the double bond is α,β to the phenyl ring and where Het is linked to the double bond via the β position;

R⁷ is hydrogen, C₁ -C₄ -alkyl, C₂ -C₄ -alkenyl, C₂ -C₄ -alkynyl, phenyl, phenyl-C₁ -C₄ -alkyl, where the alkyl, alkenyl or alkynyl radicals mentioned may be partially or fully halogenated and/or may be substituted by one or more of the following radicals:

hydroxyl, mercapto, amino, cyano, nitro, formyl, C₁ -C₄ -alkylamino, C₁ -C₄ -dialkylamino, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkylcarbonyloxy, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy;

R⁸ is hydrogen, hydroxyl, mercapto, amino, cyano, nitro, formyl, C₁ -C₄ -alkylamino, C₁ -C₄ -dialkylamino, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkylcarbonyloxy, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, where in all instances each of the alkyl radicals may be substituted by one or more of the following radicals:

cyano, formyl, C₁ -C₄ -alkylamino, C₁ -C₄ -dialkylamino, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkylcarbonyloxy, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy.

Particular preference is given to compounds of the formula Ia where R¹ is attached in position 2 and R² is attached in position 4 of the phenyl ring. ##STR14## Very particular preference is given to the compounds of the formula Ia in which the substituents R¹ and R² and Q are each as defined above, X¹ is a C₁ -C₂ -alkylene or a C₂ -alkynylene chain and

Het is a three- to six-membered, partially or fully saturated heterocyclic group or a three- to six-membered heteroaromatic group having up to three hetero atoms selected from the group consisting of:

nitrogen, oxygen and sulfur,

where the heterocyclic or heteroaromatic group mentioned may be partially or fully halogenated and/or may be substituted by R⁸.

Additionally, very particular preference is given to the compounds of the formula Ia according to the invention in which the substituents R¹, R², Q and X¹ are each as defined above and Het is a five- or six-membered, partially or fully saturated heterocyclic or a five- or six-membered heteroaromatic group having up to three hetero atoms selected from the group consisting of

nitrogen, oxygen and sulfur.

Particular preference is given to the compounds Ib of Tables 1 to 144.

                  TABLE A                                                          ______________________________________                                         No.  X.sup.1    Het                                                            ______________________________________                                         1    CH.sub.2   oxiranyl                                                         2 CH.sub.2 3-methyl-2-oxiranyl                                                 3 CH.sub.2 2-oxetanyl                                                          4 CH.sub.2 3-hydroxy-3-methyl-2-oxetanyl                                       5 CH.sub.2 3-hydroxy-3-ethyl-2-oxetanyl                                        6 CH.sub.2 3-hydroxy-3-propyl-2-oxetanyl                                       7 CH.sub.2 3-hydroxy-3-butyl-2-oxetanyl                                        8 CH.sub.2 3-methoxy-3-methyl-2-oxetanyl                                       9 CH.sub.2 3-methoxy-3-ethyl-2-oxetanyl                                        10 CH.sub.2 3-methoxy-3-propyl-2-oxetanyl                                      11 CH.sub.2 3-methoxy-3-butyl-2-oxetanyl                                       12 CH.sub.2 3-trimethylsilyloxy-3-methyl-2-oxetanyl                            13 CH.sub.2 3-trimethylsilyloxy-3-ethyl-2-oxetanyl                             14 CH.sub.2 3-trimethylsilyloxy-3-propyl-2-oxetanyl                            15 CH.sub.2 3-trimethylsilyloxy-3-butyl-2-oxetanyl                             16 CH.sub.2 3-oxetanyl                                                         17 CH.sub.2 2-furyl                                                            18 CH.sub.2 4,5-dihydro-2-furyl                                                19 CH.sub.2 2,3-dihydro-2-furyl                                                20 CH.sub.2 3-furyl                                                            21 CH.sub.2 4,5-dihydro-3-furyl                                                22 CH.sub.2 2,3-dihydro-3-furyl                                                23 CH.sub.2 2-thienyl                                                          24 CH.sub.2 4,5-dihydro-2-thienyl                                              25 CH.sub.2 2,3-dihydro-2-thienyl                                              26 CH.sub.2 5-chloro-2-thienyl                                                 27 CH.sub.2 5-methyl-2-thienyl                                                 28 CH.sub.2 3-thienyl                                                          29 CH.sub.2 4,5-dihydro-3-thienyl                                              30 CH.sub.2 2,3-dihydro-3-thienyl                                              31 CH.sub.2 2-pyrrolyl                                                         32 CH.sub.2 2,5-dihydro-2-pyrrolyl                                             33 CH.sub.2 3-pyrrole                                                          34 CH.sub.2 2,5-dihydro-3-pyrrolyl                                             35 CH.sub.2 3-isoxazolyl                                                       36 CH.sub.2 4-methyl-3-isoxazolyl                                              37 CH.sub.2 5-methyl-3-isoxazolyl                                              38 CH.sub.2 4,5-dimethyl-3-isoxazolyl                                          39 CH.sub.2 4,5-dihydro-3-isoxazolyl                                           40 CH.sub.2 4-methyl-4,5-dihydro-3-isoxazolyl                                  41 CH.sub.2 5-methyl-4,5-dihydro-3-isoxazolyl                                  42 CH.sub.2 4,5-dimethyl-4,5-dihydro-3-isoxazolyl                              43 CH.sub.2 4-isoxazolyl                                                       44 CH.sub.2 3-methyl-4-isoxazolyl                                              45 CH.sub.2 5-methyl-4-isoxazolyl                                              46 CH.sub.2 5-cyclopropyl-4-isoxazolyl                                         47 CH.sub.2 5-phenyl-4-isoxazolyl                                              48 CH.sub.2 3,5-dimethyl-4-isoxazolyl                                          49 CH.sub.2 4,5-dihydro-4-isoxazolyl                                           50 CH.sub.2 3-methyl-4,5-dihydro-4-isoxazolyl                                  51 CH.sub.2 5-methyl-4,5-dihydro-4-isoxazolyl                                  52 CH.sub.2 3,5-dimethyl-4,5-dihydro-4-isoxazolyl                              53 CH.sub.2 5-isoxazolyl                                                       54 CH.sub.2 3-methyl-5-isoxazolyl                                              55 CH.sub.2 4-methyl-5-isoxazolyl                                              56 CH.sub.2 3,4-dimethyl-5-isoxazolyl                                          57 CH.sub.2 4,5-dihydro-5-isoxazolyl                                           58 CH.sub.2 3-methyl-4,5-dihydro-5-isoxazolyl                                  59 CH.sub.2 4-methyl-4,5-dihydro-5-isoxazolyl                                  60 CH.sub.2 3,4-dimethyl-4,5-dihydro-5-isoxazolyl                              61 CH.sub.2 3-isothiazolyl                                                     62 CH.sub.2 4-methyl-3-isothiazolyl                                            63 CH.sub.2 5-methyl-3-isothiazolyl                                            64 CH.sub.2 4-isothiazolyl                                                     65 CH.sub.2 3-methyl-4-isothiazolyl                                            66 CH.sub.2 5-methyl-4-isothiazolyl                                            67 CH.sub.2 5-isothiazolyl                                                     68 CH.sub.2 3-methyl-5-isothiazolyl                                            69 CH.sub.2 4-methyl-5-isothiazolyl                                            70 CH.sub.2 2-oxazolyl                                                         71 CH.sub.2 4-oxazolyl                                                         72 CH.sub.2 5-oxazolyl                                                         73 CH.sub.2 2-thiazolyl                                                        74 CH.sub.2 4-thiazolyl                                                        75 CH.sub.2 5-thiazolyl                                                        76 CH.sub.2 3-pyrazolyl                                                        77 CH.sub.2 4-pyrazolyl                                                        78 CH.sub.2 1-methyl-3-pyrazolyl                                               79 CH.sub.2 1-methyl-4-pyrazolyl                                               80 CH.sub.2 1-methyl-5-pyrazolyl                                               81 CH.sub.2 2-imidazolyl                                                       82 CH.sub.2 1-methyl-2-imidazolyl                                              83 CH.sub.2 5-methyl-[1,3,4]-2-oxadiazolyl                                     84 CH.sub.2 5-methyl-[1,2,4]-3-oxadiazolyl                                     85 CH.sub.2 5-methyl-[1,3,4]-2-thiadiazolyl                                    86 CH.sub.2 5-methyl-[1,2,4]-3-thiadiazolyl                                    87 CH.sub.2 [1,2,4]-3-triazolyl                                                88 CH.sub.2 [1,2,3]-4-triazolyl                                                89 CH.sub.2 2-pyridyl                                                          90 CH.sub.2 6-chloro-2-pyridyl                                                 91 CH.sub.2 6-methoxy-2-pyridyl                                                92 CH.sub.2 6-trifluoromethyl-2-pyridyl                                        93 CH.sub.2 3-pyridyl                                                          94 CH.sub.2 2-chloro-3-pyridyl                                                 95 CH.sub.2 2-methoxy-3-pyridyl                                                96 CH.sub.2 4-pyridyl                                                          97 CH.sub.2 2-chloro-4-pyridyl                                                 98 CH.sub.2 2-methoxy-4-pyridyl                                                99 CH.sub.2 2-ethoxy-4-pyridyl                                                 100 CH.sub.2 2-methylthio-4-pyridyl                                            101 CH.sub.2 2-trifluoromethyl-5-pyridyl                                       102 CH.sub.2 2-pyrimidinyl                                                     103 CH.sub.2 3-pyrimidinyl                                                     104 CH.sub.2 4-pyrimidinyl                                                     105 CH.sub.2 2-pyrazinyl                                                       106 CH.sub.2 3-pyridazinyl                                                     107 CH.sub.2 4-pyridazinyl                                                     108 CH.sub.2 2-(2H-1,3-oxazinyl)                                               109 CH.sub.2 2-(6H-1,3-oxazinyl)                                               110 CH.sub.2 4-(6H-1,3-oxazinyl)                                               111 CH.sub.2 6-(6H-1,3-oxazinyl)                                               112 CH.sub.2 [1,3,5]-2-triazinyl                                               113 CH.sub.2 [1,2,4]-3-triazinyl                                               114 CH.sub.2 [1,2,4]-5-triazinyl                                               115 CH.sub.2 [1,2,4]-6-triazinyl                                               116 CHCH.sub.3 oxiranyl                                                        117 CHCH.sub.3 3-methyl-2-oxiranyl                                             118 CHCH.sub.3 2-oxetanyl                                                      119 CHCH.sub.3 3-hydroxy-3-methyl-2-oxetanyl                                   120 CHCH.sub.3 3-hydroxy-3-ethyl-2-oxetanyl                                    121 CHCH.sub.3 3-hydroxy-3-propyl-2-oxetanyl                                   122 CHCH.sub.3 3-hydroxy-3-butyl-2-oxetanyl                                    123 CHCH.sub.3 3-methoxy-3-methyl-2-oxetanyl                                   124 CHCH.sub.3 3-methoxy-3-ethyl-2-oxetanyl                                    125 CHCH.sub.3 3-methoxy-3-propyl-2-oxetanyl                                   126 CHCH.sub.3 3-methoxy-3-butyl-2-oxetanyl                                    127 CHCH.sub.3 3-trimethylsilyloxy-3-methyl-2-oxetanyl                         128 CHCH.sub.3 3-trimethylsilyloxy-3-ethyl-2-oxetanyl                          129 CHCH.sub.3 3-trimethylsilyloxy-3-propyl-2-oxetanyl                         130 CHCH.sub.3 3-trimethylsilyloxy-3-butyl-2-oxetanyl                          131 CHCH.sub.3 3-oxetanyl                                                      132 CHCH.sub.3 2-furyl                                                         133 CHCH.sub.3 4,5-dihydro-2-furyl                                             134 CHCH.sub.3 2,3-dihydro-2-furyl                                             135 CHCH.sub.3 3-furyl                                                         136 CHCH.sub.3 4,5-dihydro-3-furyl                                             137 CHCH.sub.3 2,3-dihydro-3-furyl                                             138 CHCH.sub.3 2-thienyl                                                       139 CHCH.sub.3 4,5-dihydro-2-thienyl                                           140 CHCH.sub.3 2,3-dihydro-2-thienyl                                           141 CHCH.sub.3 5-chloro-2-thienyl                                              142 CHCH.sub.3 5-methyl-2-thienyl                                              143 CHCH.sub.3 3-thienyl                                                       144 CHCH.sub.3 4,5-dihydro-3-thienyl                                           145 CHCH.sub.3 2,3-dihydro-3-thienyl                                           146 CHCH.sub.3 2-pyrrolyl                                                      147 CHCH.sub.3 2,5-dihydro-2-pyrrolyl                                          148 CHCH.sub.3 3-pyrrole                                                       149 CHCH.sub.3 2,5-dihydro-3-pyrrolyl                                          150 CHCH.sub.3 3-isoxazolyl                                                    151 CHCH.sub.3 4-methyl-3-isoxazolyl                                           152 CHCH.sub.3 5-methyl-3-isoxazolyl                                           153 CHCH.sub.3 4,5-dimethyl-3-isoxazolyl                                       154 CHCH.sub.3 4,5-dihydro-3-isoxazolyl                                        155 CHCH.sub.3 4-methyl-4,5-dihydro-3-isoxazolyl                               156 CHCH.sub.3 5-methyl-4,5-dihydro-3-isoxazolyl                               157 CHCH.sub.3 4,5-dimethyl-4,5-dihydro-3-isoxazolyl                           158 CHCH.sub.3 4-isoxazolyl                                                    159 CHCH.sub.3 3-methyl-4-isoxazolyl                                           160 CHCH.sub.3 5-methyl-4-isoxazolyl                                           161 CHCH.sub.3 5-cyclopropyl-4-isoxazolyl                                      162 CHCH.sub.3 5-phenyl-4-isoxazolyl                                           163 CHCH.sub.3 3,5-dimethyl-4-isoxazolyl                                       164 CHCH.sub.3 4,5-dihydro-4-isoxazolyl                                        165 CHCH.sub.3 3-methyl-4,5-dihydro-4-isoxazolyl                               166 CHCH.sub.3 5-methyl-4,5-dihydro-4-isoxazolyl                               167 CHCH.sub.3 3,5-dimethyl-4,5-dihydro-4-isoxazolyl                           168 CHCH.sub.3 5-isoxazolyl                                                    169 CHCH.sub.3 3-methyl-5-isoxazolyl                                           170 CHCH.sub.3 4-methyl-5-isoxazolyl                                           171 CHCH.sub.3 3,4-dimethyl-5-isoxazolyl                                       172 CHCH.sub.3 4,5-dihydro-5-isoxazolyl                                        173 CHCH.sub.3 3-methyl-4,5-dihydro-5-isoxazolyl                               174 CHCH.sub.3 4-methyl-4,5-dihydro-5-isoxazolyl                               175 CHCH.sub.3 3,4-dimethyl-4,5-dihydro-5-isoxazolyl                           176 CHCH.sub.3 3-isothiazolyl                                                  177 CHCH.sub.3 4-methyl-3-isothiazolyl                                         178 CHCH.sub.3 5-methyl-3-isothiazolyl                                         179 CHCH.sub.3 4-isothiazolyl                                                  180 CHCH.sub.3 3-methyl-4-isothiazolyl                                         181 CHCH.sub.3 5-methyl-4-isothiazolyl                                         182 CHCH.sub.3 5-isothiazolyl                                                  183 CHCH.sub.3 3-methyl-5-isothiazolyl                                         184 CHCH.sub.3 4-methyl-5-isothiazolyl                                         185 CHCH.sub.3 2-oxazolyl                                                      186 CHCH.sub.3 4-oxazolyl                                                      187 CHCH.sub.3 5-oxazolyl                                                      188 CHCH.sub.3 2-thiazolyl                                                     189 CHCH.sub.3 4-thiazolyl                                                     190 CHCH.sub.3 5-thiazolyl                                                     191 CHCH.sub.3 3-pyrazolyl                                                     192 CHCH.sub.3 4-pyrazolyl                                                     193 CHCH.sub.3 1-methyl-3-pyrazolyl                                            194 CHCH.sub.3 1-methyl-4-pyrazolyl                                            195 CHCH.sub.3 1-methyl-5-pyrazolyl                                            196 CHCH.sub.3 2-imidazolyl                                                    197 CHCH.sub.3 1-methyl-2-imidazolyl                                           198 CHCH.sub.3 5-methyl-[1,3,4]-2-oxadiazolyl                                  199 CHCH.sub.3 5-methyl-[1,2,4]-3-oxadiazolyl                                  200 CHCH.sub.3 5-methyl-[1,3,4]-2-thiadiazolyl                                 201 CHCH.sub.3 5-methyl-[1,2,4]-3-thiadiazolyl                                 202 CHCH.sub.3 [1,2,4]-3-triazolyl                                             203 CHCH.sub.3 [1,2,3]-4-triazolyl                                             204 CHCH.sub.3 2-pyridyl                                                       205 CHCH.sub.3 6-chloro-2-pyridyl                                              206 CHCH.sub.3 6-methoxy-2-pyridyl                                             207 CHCH.sub.3 6-trifluoromethyl-2-pyridyl                                     208 CHCH.sub.3 3-pyridyl                                                       209 CHCH.sub.3 2-chloro-3-pyridyl                                              210 CHCH.sub.3 2-methoxy-3-pyridyl                                             211 CHCH.sub.3 4-pyridyl                                                       212 CHCH.sub.3 2-chloro-4-pyridyl                                              213 CHCH.sub.3 2-methoxy-4-pyridyl                                             214 CHCH.sub.3 2-ethoxy-4-pyridyl                                              215 CHCH.sub.3 2-methylthio-4-pyridyl                                          216 CHCH.sub.3 2-trifluoromethyl-5-pyridyl                                     217 CHCH.sub.3 2-pyrimidinyl                                                   218 CHCH.sub.3 3-pyrimidinyl                                                   219 CHCH.sub.3 4-pyrimidinyl                                                   220 CHCH.sub.3 2-pyrazinyl                                                     221 CHCH.sub.3 3-pyridazinyl                                                   222 CHCH.sub.3 4-pyridazinyl                                                   223 CHCH.sub.3 2-(2H-1,3-oxazinyl)                                             224 CHCH.sub.3 2-(6H-1,3-oxazinyl)                                             225 CHCH.sub.3 4-(6H-1,3-oxazinyl)                                             226 CHCH.sub.3 6-(6H-1,3-oxazinyl)                                             227 CHCH.sub.3 [1,3,5]-2-triazinyl                                             228 CHCH.sub.3 [1,2,4]-3-triazinyl                                             229 CHCH.sub.3 [1,2,4]-5-triazinyl                                             230 CHCH.sub.3 [1,2,4]-6-triazinyl                                             231 CHOH oxiranyl                                                              232 CHOH 3-methyl-2-oxiranyl                                                   233 CHOH 2-oxetanyl                                                            234 CHOH 3-hydroxy-3-methyl-2-oxetanyl                                         235 CHOH 3-hydroxy-3-ethyl-2-oxetanyl                                          236 CHOH 3-hydroxy-3-propyl-2-oxetanyl                                         237 CHOH 3-hydroxy-3-butyl-2-oxetanyl                                          238 CHOH 3-methoxy-3-methyl-2-oxetanyl                                         239 CHOH 3-methoxy-3-ethyl-2-oxetanyl                                          240 CHOH 3-methoxy-3-propyl-2-oxetanyl                                         241 CHOH 3-methoxy-3-butyl-2-oxetanyl                                          242 CHOH 3-trimethylsilyloxy-3-methyl-2-oxetanyl                               243 CHOH 3-trimethylsilyloxy-3-ethyl-2-oxetanyl                                244 CHOH 3-trimethylsilyloxy-3-propyl-2-oxetanyl                               245 CHOH 3-trimethylsilyloxy-3-butyl-2-oxetanyl                                246 CHOH 3-oxetanyl                                                            247 CHOH 2-furyl                                                               248 CHOH 4,5-dihydro-2-furyl                                                   249 CHOH 2,3-dihydro-2-furyl                                                   250 CHOH 3-furyl                                                               251 CHOH 4,5-dihydro-3-furyl                                                   252 CHOH 2,3-dihydro-3-furyl                                                   253 CHOH 2-thienyl                                                             254 CHOH 4,5-dihydro-2-thienyl                                                 255 CHOH 2,3-dihydro-2-thienyl                                                 256 CHOH 5-chloro-2-thienyl                                                    257 CHOH 5-methyl-2-thienyl                                                    258 CHOH 3-thienyl                                                             259 CHOH 4,5-dihydro-3-thienyl                                                 260 CHOH 2,3-dihydro-3-thienyl                                                 261 CHOH 2-pyrrolyl                                                            262 CHOH 2,5-dihydro-2-pyrrolyl                                                263 CHOH 3-pyrrole                                                             264 CHOH 2,5-dihydro-3-pyrrolyl                                                265 CHOH 3-isoxazolyl                                                          266 CHOH 4-methyl-3-isoxazolyl                                                 267 CHOH 5-methyl-3-isoxazolyl                                                 268 CHOH 4,5-dimethyl-3-isoxazolyl                                             269 CHOH 4,5-dihydro-3-isoxazolyl                                              270 CHOH 4-methyl-4,5-dihydro-3-isoxazolyl                                     271 CHOH 5-methyl-4,5-dihydro-3-isoxazolyl                                     272 CHOH 4,5-dimethyl-4,5-dihydro-3-isoxazolyl                                 273 CHOH 4-isoxazolyl                                                          274 CHOH 3-methyl-4-isoxazolyl                                                 275 CHOH 5-methyl-4-isoxazolyl                                                 276 CHOH 5-cyclopropyl-4-isoxazolyl                                            277 CHOH 5-phenyl-4-isoxazolyl                                                 278 CHOH 3,5-dimethyl-4-isoxazolyl                                             279 CHOH 4,5-dihydro-4-isoxazolyl                                              280 CHOH 3-methyl-4,5-dihydro-4-isoxazolyl                                     281 CHOH 5-methyl-4,5-dihydro-4-isoxazolyl                                     282 CHOH 3,5-dimethyl-4,5-dihydro-4-isoxazolyl                                 283 CHOH 5-isoxazolyl                                                          284 CHOH 3-methyl-5-isoxazolyl                                                 285 CHOH 4-methyl-5-isoxazolyl                                                 286 CHOH 3,4-dimethyl-5-isoxazolyl                                             287 CHOH 4,5-dihydro-5-isoxazolyl                                              288 CHOH 3-methyl-4,5-dihydro-5-isoxazolyl                                     289 CHOH 4-methyl-4,5-dihydro-5-isoxazolyl                                     290 CHOH 3,4-dimethyl-4,5-dihydro-5-isoxazolyl                                 291 CHOH 3-isothiazolyl                                                        292 CHOH 4-methyl-3-isothiazolyl                                               293 CHOH 5-methyl-3-isothiazolyl                                               294 CHOH 4-isothiazolyl                                                        295 CHOH 3-methyl-4-isothiazolyl                                               296 CHOH 5-methyl-4-isothiazolyl                                               297 CHOH 5-isothiazolyl                                                        298 CHOH 3-methyl-5-isothiazolyl                                               299 CHOH 4-methyl-5-isothiazolyl                                               300 CHOH 2-oxazolyl                                                            301 CHOH 4-oxazolyl                                                            302 CHOH 5-oxazolyl                                                            303 CHOH 2-thiazolyl                                                           304 CHOH 4-thiazolyl                                                           305 CHOH 5-thiazolyl                                                           306 CHOH 3-pyrazolyl                                                           307 CHOH 4-pyrazolyl                                                           308 CHOH 1-methyl-3-pyrazolyl                                                  309 CHOH 1-methyl-4-pyrazolyl                                                  310 CHOH 1-methyl-5-pyrazolyl                                                  311 CHOH 2-imidazolyl                                                          312 CHOH 1-methyl-2-imidazolyl                                                 313 CHOH 5-methyl-[1,3,4]-2-oxadiazolyl                                        314 CHOH 5-methyl-[1,2,4]-3-oxadiazolyl                                        315 CHOH 5-methyl-[1,3,4]-2-thiadiazolyl                                       316 CHOH 5-methyl-[1,2,4]-3-thiadiazolyl                                       317 CHOH [1,2,4]-3-triazolyl                                                   318 CHOH [1,2,3]-4-triazolyl                                                   319 CHOH 2-pyridyl                                                             320 CHOH 6-chloro-2-pyridyl                                                    321 CHOH 6-methoxy-2-pyridyl                                                   322 CHOH 6-trifluoromethyl-2-pyridyl                                           323 CHOH 3-pyridyl                                                             324 CHOH 2-chloro-3-pyridyl                                                    325 CHOH 2-methoxy-3-pyridyl                                                   326 CHOH 4-pyridyl                                                             327 CHOH 2-chloro-4-pyridyl                                                    328 CHOH 2-methoxy-4-pyridyl                                                   329 CHOH 2-ethoxy-4-pyridyl                                                    330 CHOH 2-methylthio-4-pyridyl                                                331 CHOH 2-trifluoromethyl-5-pyridyl                                           332 CHOH 2-pyrimidinyl                                                         333 CHOH 3-pyrimidinyl                                                         334 CHOH 4-pyrimidinyl                                                         335 CHOH 2-pyrazinyl                                                           336 CHOH 3-pyridazinyl                                                         337 CHOH 4-pyridazinyl                                                         338 CHOH 2-(2H-1,3-oxazinyl)                                                   339 CHOH 2-(6H-1,3-oxazinyl)                                                   340 CHOH 4-(6H-1,3-oxazinyl)                                                   341 CHOH 6-(6H-1,3-oxazinyl)                                                   342 CHOH [1,3,5]-2-triazinyl                                                   343 CHOH [1,2,4]-3-triazinyl                                                   344 CHOH [1,2,4]-5-triazinyl                                                   345 CHOH [1,2,4]-6-triazinyl                                                   346 CHOCH.sub.3 oxiranyl                                                       347 CHOCH.sub.3 3-methyl-2-oxiranyl                                            348 CHOCH.sub.3 2-oxetanyl                                                     349 CHOCH.sub.3 3-hydroxy-3-methyl-2-oxetanyl                                  350 CHOCH.sub.3 3-hydroxy-3-ethyl-2-oxetanyl                                   351 CHOCH.sub.3 3-hydroxy-3-propyl-2-oxetanyl                                  352 CHOCH.sub.3 3-hydroxy-3-butyl-2-oxetanyl                                   353 CHOCH.sub.3 3-methoxy-3-methyl-2-oxetanyl                                  354 CHOCH.sub.3 3-methoxy-3-ethyl-2-oxetanyl                                   355 CHOCH.sub.3 3-methoxy-3-propyl-2-oxetanyl                                  356 CHOCH.sub.3 3-methoxy-3-butyl-2-oxetanyl                                   357 CHOCH.sub.3 3-trimethylsilyloxy-3-methyl-2-oxetanyl                        358 CHOCH.sub.3 3-trimethylsilyloxy-3-ethyl-2-oxetanyl                         359 CHOCH.sub.3 3-trimethylsilyloxy-3-propyl-2-oxetanyl                        360 CHOCH.sub.3 3-trimethylsilyloxy-3-butyl-2-oxetanyl                         361 CHOCH.sub.3 3-oxetanyl                                                     362 CHOCH.sub.3 2-furyl                                                        363 CHOCH.sub.3 4,5-dihydro-2-furyl                                            364 CHOCH.sub.3 2,3-dihydro-2-furyl                                            365 CHOCH.sub.3 3-furyl                                                        366 CHOCH.sub.3 4,5-dihydro-3-furyl                                            367 CHOCH.sub.3 2,3-dihydro-3-furyl                                            368 CHOCH.sub.3 2-thienyl                                                      369 CHOCH.sub.3 4,5-dihydro-2-thienyl                                          370 CHOCH.sub.3 2,3-dihydro-2-thienyl                                          371 CHOCH.sub.3 5-chloro-2-thienyl                                             372 CHOCH.sub.3 5-methyl-2-thienyl                                             373 CHOCH.sub.3 3-thienyl                                                      374 CHOCH.sub.3 4,5-dihydro-3-thienyl                                          375 CHOCH.sub.3 2,3-dihydro-3-thienyl                                          376 CHOCH.sub.3 2-pyrrolyl                                                     377 CHOCH.sub.3 2,5-dihydro-2-pyrrolyl                                         378 CHOCH.sub.3 3-pyrrole                                                      379 CHOCH.sub.3 2,5-dihydro-3-pyrrolyl                                         380 CHOCH.sub.3 3-isoxazolyl                                                   381 CHOCH.sub.3 4-methyl-3-isoxazolyl                                          382 CHOCH.sub.3 5-methyl-3-isoxazolyl                                          383 CHOCH.sub.3 4,5-dimethyl-3-isoxazolyl                                      384 CHOCH.sub.3 4,5-dihydro-3-isoxazolyl                                       385 CHOCH.sub.3 4-methyl-4,5-dihydro-3-isoxazolyl                              386 CHOCH.sub.3 5-methyl-4,5-dihydro-3-isoxazolyl                              387 CHOCH.sub.3 4,5-dimethyl-4,5-dihydro-3-isoxazolyl                          388 CHOCH.sub.3 4-isoxazolyl                                                   389 CHOCH.sub.3 3-methyl-4-isoxazolyl                                          390 CHOCH.sub.3 5-methyl-4-isoxazolyl                                          391 CHOCH.sub.3 5-cyclopropyl-4-isoxazolyl                                     392 CHOCH.sub.3 5-phenyl-4-isoxazolyl                                          393 CHOCH.sub.3 3,5-dimethyl-4-isoxazolyl                                      394 CHOCH.sub.3 4,5-dihydro-4-isoxazolyl                                       395 CHOCH.sub.3 3-methyl-4,5-dihydro-4-isoxazolyl                              396 CHOCH.sub.3 5-methyl-4,5-dihydro-4-isoxazolyl                              397 CHOCH.sub.3 3,5-dimethyl-4,5-dihydro-4-isoxazolyl                          398 CHOCH.sub.3 5-isoxazolyl                                                   399 CHOCH.sub.3 3-methyl-5-isoxazolyl                                          400 CHOCH.sub.3 4-methyl-5-isoxazolyl                                          401 CHOCH.sub.3 3,4-dimethyl-5-isoxazolyl                                      402 CHOCH.sub.3 4,5-dihydro-5-isoxazolyl                                       403 CHOCH.sub.3 3-methyl-4,5-dihydro-5-isoxazolyl                              404 CHOCH.sub.3 4-methyl-4,5-dihydro-5-isoxazolyl                              405 CHOCH.sub.3 3,4-dimethyl-4,5-dihydro-5-isoxazolyl                          406 CHOCH.sub.3 3-isothiazolyl                                                 407 CHOCH.sub.3 4-methyl-3-isothiazolyl                                        408 CHOCH.sub.3 5-methyl-3-isothiazolyl                                        409 CHOCH.sub.3 4-isothiazolyl                                                 410 CHOCH.sub.3 3-methyl-4-isothiazolyl                                        411 CHOCH.sub.3 5-methyl-4-isothiazotyl                                        412 CHOCH.sub.3 5-isothiazolyl                                                 413 CHOCH.sub.3 3-methyl-5-isothiazolyl                                        414 CHOCH.sub.3 4-methyl-5-isothiazolyl                                        415 CHOCH.sub.3 2-oxazolyl                                                     416 CHOCH.sub.3 4-oxazolyl                                                     417 CHOCH.sub.3 5-oxazolyl                                                     418 CHOCH.sub.3 2-thiazolyl                                                    419 CHOCH.sub.3 4-thiazolyl                                                    420 CHOCH.sub.3 5-thiazolyl                                                    421 CHOCH.sub.3 3-pyrazolyl                                                    422 CHOCH.sub.3 4-pyrazolyl                                                    423 CHOCH.sub.3 1-methyl-3-pyrazolyl                                           424 CHOCH.sub.3 1-methyl-4-pyrazolyl                                           425 CHOCH.sub.3 1-methyl-5-pyrazolyl                                           426 CHOCH.sub.3 2-imidazolyl                                                   427 CHOCH.sub.3 1-methyl-2-imidazolyl                                          428 CHOCH.sub.3 5-methyl-[1,3,4]-2-oxadiazolyl                                 429 CHOCH.sub.3 5-methyl-[1,2,4]-3-oxadiazolyl                                 430 CHOCH.sub.3 5-methyl-[1,3,4]-2-thiadiazolyl                                431 CHOCH.sub.3 5-methyl-[1,2,4]-3-thiadiazolyl                                432 CHOCH.sub.3 [1,2,4]-3-triazolyl                                            433 CHOCH.sub.3 [1,2,3]-4-triazolyl                                            434 CHOCH.sub.3 2-pyridyl                                                      435 CHOCH.sub.3 6-chloro-2-pyridyl                                             436 CHOCH.sub.3 6-methoxy-2-pyridyl                                            437 CHOCH.sub.3 6-trifluoromethyl-2-pyridyl                                    438 CHOCH.sub.3 3-pyridyl                                                      439 CHOCH.sub.3 2-chloro-3-pyridyl                                             440 CHOCH.sub.3 2-methoxy-3-pyridyl                                            441 CHOCH.sub.3 4-pyridyl                                                      442 CHOCH.sub.3 2-chloro-4-pyridyl                                             443 CHOCH.sub.3 2-methoxy-4-pyridyl                                            444 CHOCH.sub.3 2-ethoxy-4-pyridyl                                             445 CHOCH.sub.3 2-methylthio-4-pyridyl                                         446 CHOCH.sub.3 2-trifluoromethyl-5-pyridyl                                    447 CHOCH.sub.3 2-pyrimidinyl                                                  448 CHOCH.sub.3 3-pyrimidinyl                                                  449 CHOCH.sub.3 4-pyrimidinyl                                                  450 CHOCH.sub.3 2-pyrazinyl                                                    451 CHOCH.sub.3 3-pyridazinyl                                                  452 CHOCH.sub.3 4-pyridazinyl                                                  453 CHOCH.sub.3 2-(2H-1,3-oxazinyl)                                            454 CHOCH.sub.3 2-(6H-1,3-oxazinyl)                                            455 CHOCH.sub.3 4-(6H-1,3-oxazinyl)                                            456 CHOCH.sub.3 6-(6H-1,3-oxazinyl)                                            457 CHOCH.sub.3 [1,3,5]-2-triazinyl                                            458 CHOCH.sub.3 [1,2,4]-3-triazinyl                                            459 CHOCH.sub.3 [1,2,4]-5-triazinyl                                            460 CHOCH.sub.3 [1,2,4]-6-triazinyl                                            461 CHOCOCH.sub.3 oxiranyl                                                     462 CHOCOCH.sub.3 3-methyl-2-oxiranyl                                          463 CHOCOCH.sub.3 2-oxetanyl                                                   464 CHOCOCH.sub.3 3-hydroxy-3-methyl-2-oxetanyl                                465 CHOCOCH.sub.3 3-hydroxy-3-ethyl-2-oxetanyl                                 466 CHOCOCH.sub.3 3-hydroxy-3-propyl-2-oxetanyl                                467 CHOCOCH.sub.3 3-hydroxy-3-butyl-2-oxetanyl                                 468 CHOCOCH.sub.3 3-methoxy-3-methyl-2-oxetanyl                                469 CHOCOCH.sub.3 3-methoxy-3-ethyl-2-oxetanyl                                 470 CHOCOCH.sub.3 3-methoxy-3-propyl-2-oxetanyl                                471 CHOCOCH.sub.3 3-methoxy-3-butyl-2-oxetanyl                                 472 CHOCOCH.sub.3 3-trimethylsilyloxy-3-methyl-2-oxetanyl                      473 CHOCOCH.sub.3 3-trimethylsilyloxy-3-ethyl-2-oxetanyl                       474 CHOCOCH.sub.3 3-trimethylsilyloxy-3-propyl-2-oxetanyl                      475 CHOCOCH.sub.3 3-trimethylsilyloxy-3-butyl-2-oxetanyl                       476 CHOCOCH.sub.3 3-oxetanyl                                                   477 CHOCOCH.sub.3 2-furyl                                                      478 CHOCOCH.sub.3 4,5-dihydro-2-furyl                                          479 CHOCOCH.sub.3 2,3-dihydro-2-furyl                                          480 CHOCOCH.sub.3 3-furyl                                                      481 CHOCOCH.sub.3 4,5-dihydro-3-furyl                                          482 CHOCOCH.sub.3 2,3-dihydro-3-furyl                                          483 CHOCOCH.sub.3 2-thienyl                                                    484 CHOCOCH.sub.3 4,5-dihydro-2-thienyl                                        485 CHOCOCH.sub.3 2,3-dihydro-2-thienyl                                        486 CHOCOCH.sub.3 5-chloro-2-thienyl                                           487 CHOCOCH.sub.3 5-methyl-2-thienyl                                           488 CHOCOCH.sub.3 3-thienyl                                                    489 CHOCOCH.sub.3 4,5-dihydro-3-thienyl                                        490 CHOCOCH.sub.3 2,3-dihydro-3-thienyl                                        491 CHOCOCH.sub.3 2-pyrrolyl                                                   492 CHOCOCH.sub.3 2,5-dihydro-2-pyrrolyl                                       493 CHOCOCH.sub.3 3-pyrrole                                                    494 CHOCOCH.sub.3 2,5-dihydro-3-pyrrolyl                                       495 CHOCOCH.sub.3 3-isoxazolyl                                                 496 CHOCOCH.sub.3 4-methyl-3-isoxazolyl                                        497 CHOCOCH.sub.3 5-methyl-3-isoxazolyl                                        498 CHOCOCH.sub.3 4,5-dimethyl-3-isoxazolyl                                    499 CHOCOCH.sub.3 4,5-dihydro-3-isoxazolyl                                     500 CHOCOCH.sub.3 4-methyl-4,5-dihydro-3-isoxazolyl                            501 CHOCOCH.sub.3 5-methyl-4,5-dihydro-3-isoxazolyl                            502 CHOCOCH.sub.3 4,5-dimethyl-4,5-dihydro-3-isoxazolyl                        503 CHOCOCH.sub.3 4-isoxazolyl                                                 504 CHOCOCH.sub.3 3-methyl-4-isoxazolyl                                        505 CHOCOCH.sub.3 5-methyl-4-isoxazolyl                                        506 CHOCOCH.sub.3 5-cyclopropyl-4-isoxazolyl                                   507 CHOCOCH.sub.3 5-phenyl-4-isoxazolyl                                        508 CHOCOCH.sub.3 3,5-dimethyl-4-isoxazolyl                                    509 CHOCOCH.sub.3 4,5-dihydro-4-isoxazolyl                                     510 CHOCOCH.sub.3 3-methyl-4,5-dihydro-4-isoxazolyl                            511 CHOCOCH.sub.3 5-methyl-4,5-dihydro-4-isoxazolyl                            512 CHOCOCH.sub.3 3,5-dimethyl-4,5-dihydro-4-isoxazolyl                        513 CHOCOCH.sub.3 5-isoxazolyl                                                 514 CHOCOCH.sub.3 3-methyl-5-isoxazolyl                                        515 CHOCOCH.sub.3 4-methyl-5-isoxazolyl                                        516 CHOCOCH.sub.3 3,4-dimethyl-5-isoxazolyl                                    517 CHOCOCH.sub.3 4,5-dihydro-5-isoxazolyl                                     518 CHOCOCH.sub.3 3-methyl-4,5-dihydro-5-isoxazolyl                            519 CHOCOCH.sub.3 4-methyl-4,5-dihydro-5-isoxazolyl                            520 CHOCOCH.sub.3 3,4-dimethyl-4,5-dihydro-5-isoxazolyl                        521 CHOCOCH.sub.3 3-isothiazolyl                                               522 CHOCOCH.sub.3 4-methyl-3-isothiazolyl                                      523 CHOCOCH.sub.3 5-methyl-3-isothiazolyl                                      524 CHOCOCH.sub.3 4-isothiazolyl                                               525 CHOCOCH.sub.3 3-methyl-4-isothiazolyl                                      526 CHOCOCH.sub.3 5-methyl-4-isothiazolyl                                      527 CHOCOCH.sub.3 5-isothiazolyl                                               528 CHOCOCH.sub.3 3-methyl-5-isothiazolyl                                      529 CHOCOCH.sub.3 4-methyl-5-isothiazolyl                                      530 CHOCOCH.sub.3 2-oxazolyl                                                   531 CHOCOCH.sub.3 4-oxazolyl                                                   532 CHOCOCH.sub.3 5-oxazolyl                                                   533 CHOCOCH.sub.3 2-thiazolyl                                                  534 CHOCOCH.sub.3 4-thiazolyl                                                  535 CHOCOCH.sub.3 5-thiazolyl                                                  536 CHOCOCH.sub.3 3-pyrazolyl                                                  537 CHOCOCH.sub.3 4-pyrazolyl                                                  538 CHOCOCH.sub.3 1-methyl-3-pyrazolyl                                         539 CHOCOCH.sub.3 1-methyl-4-pyrazolyl                                         540 CHOCOCH.sub.3 1-methyl-5-pyrazolyl                                         541 CHOCOCH.sub.3 2-imidazolyl                                                 542 CHOCOCH.sub.3 1-methyl-2-imidazolyl                                        543 CHOCOCH.sub.3 5-methyl-[1,3,4]-2-oxadiazolyl                               544 CHOCOCH.sub.3 5-methyl-[1,2,4]-3-oxadiazolyl                               545 CHOCOCH.sub.3 5-methyl-[1,3,4]-2-thiadiazolyl                              546 CHOCOCH.sub.3 5-methyl-[1,2,4]-3-thiadiazolyl                              547 CHOCOCH.sub.3 [1,2,4]-3-triazolyl                                          548 CHOCOCH.sub.3 [1,2,3]-4-triazolyl                                          549 CHOCOCH.sub.3 2-pyridyl                                                    550 CHOCOCH.sub.3 6-chloro-2-pyridyl                                           551 CHOCOCH.sub.3 6-methoxy-2-pyridyl                                          552 CHOCOCH.sub.3 6-trifluoromethyl-2-pyridyl                                  553 CHOCOCH.sub.3 3-pyridyl                                                    554 CHOCOCH.sub.3 2-chloro-3-pyridyl                                           555 CHOCOCH.sub.3 2-methoxy-3-pyridyl                                          556 CHOCOCH.sub.3 4-pyridyl                                                    557 CHOCOCH.sub.3 2-chloro-4-pyridyl                                           558 CHOCOCH.sub.3 2-methoxy-4-pyridyl                                          559 CHOCOCH.sub.3 2-ethoxy-4-pyridyl                                           560 CHOCOCH.sub.3 2-methylthio-4-pyridyl                                       561 CHOCOCH.sub.3 2-trifluoromethyl-5-pyridyl                                  562 CHOCOCH.sub.3 2-pyrimidinyl                                                563 CHOCOCH.sub.3 3-pyrimidinyl                                                564 CHOCOCH.sub.3 4-pyrimidinyl                                                565 CHOCOCH.sub.3 2-pyrazinyl                                                  566 CHOCOCH.sub.3 3-pyridazinyl                                                567 CHOCOCH.sub.3 4-pyridazinyl                                                568 CHOCOCH.sub.3 2-(2H-1,3-oxazinyl)                                          569 CHOCOCH.sub.3 2-(6H-1,3-oxazinyl)                                          570 CHOCOCH.sub.3 4-(6H-1,3-oxazinyl)                                          571 CHOCOCH.sub.3 6-(6H-1,3-oxazinyl)                                          572 CHOCOCH.sub.3 [1,3,5]-2-triazinyl                                          573 CHOCOCH.sub.3 [1,2,4]-3-triazinyl                                          574 CHOCOCH.sub.3 [1,2,4]-5-triazinyl                                          575 CHOCOCH.sub.3 [1,2,4]-6-triazinyl                                          576 CHOSO.sub.2 CH.sub.3 oxiranyl                                              577 CHOSO.sub.2 CH.sub.3 3-methyl-2-oxiranyl                                   578 CHOSO.sub.2 CH.sub.3 2-oxetanyl                                            579 CHOSO.sub.2 CH.sub.3 3-hydroxy-3-methyl-2-oxetanyl                         580 CHOSO.sub.2 CH.sub.3 3-hydroxy-3-ethyl-2-oxetanyl                          581 CHOSO.sub.2 CH.sub.3 3-hydroxy-3-propyl-2-oxetanyl                         582 CHOSO.sub.2 CH.sub.3 3-hydroxy-3-butyl-2-oxetanyl                          583 CHOSO.sub.2 CH.sub.3 3-methoxy-3-methyl-2-oxetanyl                         584 CHOSO.sub.2 CH.sub.3 3-methoxy-3-ethyl-2-oxetanyl                          585 CHOSO.sub.2 CH.sub.3 3-methoxy-3-propyl-2-oxetanyl                         586 CHOSO.sub.2 CH.sub.3 3-methoxy-3-butyl-2-oxetanyl                          587 CHOSO.sub.2 CH.sub.3 3-trimethylsilyloxy-3-methyl-2-oxetanyl                              588 CHOSO.sub.2 CH.sub.3 3-trimethylsilyloxy-3-ethyl-2-ox                     etanyl                                                           589 CHOSO.sub.2 CH.sub.3 3-trimethylsilyloxy-3-propyl-2-oxetanyl                              590 CHOSO.sub.2 CH.sub.3 3-trimethylsilyloxy-3-butyl-2-ox                     etanyl                                                           591 CHOSO.sub.2 CH.sub.3 3-oxetanyl                                            592 CHOSO.sub.2 CH.sub.3 2-furyl                                               593 CHOSO.sub.2 CH.sub.3 4,5-dihydro-2-furyl                                   594 CHOSO.sub.2 CH.sub.3 2,3-dihydro-2-furyl                                   595 CHOSO.sub.2 CH.sub.3 3-furyl                                               596 CHOSO.sub.2 CH.sub.3 4,5-dihydro-3-furyl                                   597 CHOSO.sub.2 CH.sub.3 2,3-dihydro-3-furyl                                   598 CHOSO.sub.2 CH.sub.3 2-thienyl                                             599 CHOSO.sub.2 CH.sub.3 4,5-dihydro-2-thienyl                                 600 CHOSO.sub.2 CH.sub.3 2,3-dihydro-2-thienyl                                 601 CHOSO.sub.2 CH.sub.3 5-chloro-2-thienyl                                    602 CHOSO.sub.2 CH.sub.3 5-methyl-2-thienyl                                    603 CHOSO.sub.2 CH.sub.3 3-thienyl                                             604 CHOSO.sub.2 CH.sub.3 4,5-dihydro-3-thienyl                                 605 CHOSO.sub.2 CH.sub.3 2,3-dihydro-3-thienyl                                 606 CHOSO.sub.2 CH.sub.3 2-pyrrolyl                                            607 CHOSO.sub.2 CH.sub.3 2,5-dihydro-2-pyrrolyl                                608 CHOSO.sub.2 CH.sub.3 3-pyrrole                                             609 CHOSO.sub.2 CH.sub.3 2,5-dihydro-3-pyrrolyl                                610 CHOSO.sub.2 CH.sub.3 3-isoxazolyl                                          611 CHOSO.sub.2 CH.sub.3 4-methyl-3-isoxazolyl                                 612 CHOSO.sub.2 CH.sub.3 5-methyl-3-isoxazolyl                                 613 CHOSO.sub.2 CH.sub.3 4,5-dimethyl-3-isoxazolyl                             614 CHOSO.sub.2 CH.sub.3 4,5-dihydro-3-isoxazolyl                              615 CHOSO.sub.2 CH.sub.3 4-methyl-4,5-dihydro-3-isoxazolyl                     616 CHOSO.sub.2 CH.sub.3 5-methyl-4,5-dihydro-3-isoxazolyl                     617 CHOSO.sub.2 CH.sub.3 4,5-dimethyl-4,5-dihydro-3-isoxazolyl                 618 CHOSO.sub.2 CH.sub.3 4-isoxazolyl                                          619 CHOSO.sub.2 CH.sub.3 3-methyl-4-isoxazolyl                                 620 CHOSO.sub.2 CH.sub.3 5-methyl-4-isoxazolyl                                 621 CHOSO.sub.2 CH.sub.3 5-cyclopropyl-4-isoxazolyl                            622 CHOSO.sub.2 CH.sub.3 5-phenyl-4-isoxazolyl                                 623 CHOSO.sub.2 CH.sub.3 3,5-dimethyl-4-isoxazolyl                             624 CHOSO.sub.2 CH.sub.3 4,5-dihydro-4-isoxazolyl                              625 CHOSO.sub.2 CH.sub.3 3-methyl-4,5-dihydro-4-isoxazolyl                     626 CHOSO.sub.2 CH.sub.3 5-methyl-4,5-dihydro-4-isoxazolyl                     627 CHOSO.sub.2 CH.sub.3 3,5-dimethyl-4,5-dihydro-4-isoxazolyl                 628 CHOSO.sub.2 CH.sub.3 5-isoxazolyl                                          629 CHOSO.sub.2 CH.sub.3 3-methyl-5-isoxazolyl                                 630 CHOSO.sub.2 CH.sub.3 4-methyl-5-isoxazolyl                                 631 CHOSO.sub.2 CH.sub.3 3,4-dimethyl-5-isoxazolyl                             632 CHOSO.sub.2 CH.sub.3 4,5-dihydro-5-isoxazolyl                              633 CHOSO.sub.2 CH.sub.3 3-methyl-4,5-dihydro-5-isoxazolyl                     634 CHOSO.sub.2 CH.sub.3 4-methyl-4,5-dihydro-5-isoxazolyl                     635 CHOSO.sub.2 CH.sub.3 3,4-dimethyl-4,5-dihydro-5-isoxazolyl                 636 CHOSO.sub.2 CH.sub.3 3-isothiazolyl                                        637 CHOSO.sub.2 CH.sub.3 4-methyl-3-isothiazolyl                               638 CHOSO.sub.2 CH.sub.3 5-methyl-3-isothiazolyl                               639 CHOSO.sub.2 CH.sub.3 4-isothiazolyl                                        640 CHOSO.sub.2 CH.sub.3 3-methyl-4-isothiazolyl                               641 CHOSO.sub.2 CH.sub.3 5-methyl-4-isothiazolyl                               642 CHOSO.sub.2 CH.sub.3 5-isothiazolyl                                        643 CHOSO.sub.2 CH.sub.3 3-methyl-5-isothiazolyl                               644 CHOSO.sub.2 CH.sub.3 4-methyl-5-isothiazolyl                               645 CHOSO.sub.2 CH.sub.3 2-oxazolyl                                            646 CHOSO.sub.2 CH.sub.3 4-oxazolyl                                            647 CHOSO.sub.2 CH.sub.3 5-oxazolyl                                            648 CHOSO.sub.2 CH.sub.3 2-thiazolyl                                           649 CHOSO.sub.2 CH.sub.3 4-thiazolyl                                           650 CHOSO.sub.2 CH.sub.3 5-thiazolyl                                           651 CHOSO.sub.2 CH.sub.3 3-pyrazolyl                                           652 CHOSO.sub.2 CH.sub.3 4-pyrazolyl                                           653 CHOSO.sub.2 CH.sub.3 1-methyl-3-pyrazolyl                                  654 CHOSO.sub.2 CH.sub.3 1-methyl-4-pyrazolyl                                  655 CHOSO.sub.2 CH.sub.3 1-methyl-5-pyrazolyl                                  656 CHOSO.sub.2 CH.sub.3 2-imidazolyl                                          657 CHOSO.sub.2 CH.sub.3 1-methyl-2-imidazolyl                                 658 CHOSO.sub.2 CH.sub.3 5-methyl-[1,3,4]-2-oxadiazolyl                        659 CHOSO.sub.2 CH.sub.3 5-methyl-[1,2,4]-3-oxadiazolyl                        660 CHOSO.sub.2 CH.sub.3 5-methyl-[1,3,4]-2-thiadiazolyl                       661 CHOSO.sub.2 CH.sub.3 5-methyl-[1,2,4]-3-thiadiazolyl                       662 CHOSO.sub.2 CH.sub.3 [1,2,4]-3-triazolyl                                   663 CHOSO.sub.2 CH.sub.3 [1,2,3]-4-triazolyl                                   664 CHOSO.sub.2 CH.sub.3 2-pyridyl                                             665 CHOSO.sub.2 CH.sub.3 6-chloro-2-pyridyl                                    666 CHOSO.sub.2 CH.sub.3 6-methoxy-2-pyridyl                                   667 CHOSO.sub.2 CH.sub.3 6-trifluoromethyl-2-pyridyl                           668 CHOSO.sub.2 CH.sub.3 3-pyridyl                                             669 CHOSO.sub.2 CH.sub.3 2-chloro-3-pyridyl                                    670 CHOSO.sub.2 CH.sub.3 2-methoxy-3-pyridyl                                   671 CHOSO.sub.2 CH.sub.3 4-pyridyl                                             672 CHOSO.sub.2 CH.sub.3 2-chloro-4-pyridyl                                    673 CHOSO.sub.2 CH.sub.3 2-methoxy-4-pyridyl                                   674 CHOSO.sub.2 CH.sub.3 2-ethoxy-4-pyridyl                                    675 CHOSO.sub.2 CH.sub.3 2-methylthio-4-pyridyl                                676 CHOSO.sub.2 CH.sub.3 2-trifluoromethyl-5-pyridyl                           677 CHOSO.sub.2 CH.sub.3 2-pyrimidinyl                                         678 CHOSO.sub.2 CH.sub.3 3-pyrimidinyl                                         679 CHOSO.sub.2 CH.sub.3 4-pyrimidinyl                                         680 CHOSO.sub.2 CH.sub.3 2-pyrazinyl                                           681 CHOSO.sub.2 CH.sub.3 3-pyridazinyl                                         682 CHOSO.sub.2 CH.sub.3 4-pyridazinyl                                         683 CHOSO.sub.2 CH.sub.3 2-(2H-1,3-oxazinyl)                                   684 CHOSO.sub.2 CH.sub.3 2-(6H-1,3-oxazinyl)                                   685 CHOSO.sub.2 CH.sub.3 4-(6H-1,3-oxazinyl)                                   686 CHOSO.sub.2 CH.sub.3 6-(6H-1,3-oxazinyl)                                   687 CHOSO.sub.2 CH.sub.3 [1,3,5]-2-triazinyl                                   688 CHOSO.sub.2 CH.sub.3 [1,2,4]-3-triazinyl                                   689 CHOSO.sub.2 CH.sub.3 [1,2,4]-5-triazinyl                                   690 CHOSO.sub.2 CH.sub.3 [1,2,4]-6-triazinyl                                   691 CH.sub.2 CH.sub.2 oxiranyl                                                 692 CH.sub.2 CH.sub.2 3-methyl-2-oxiranyl                                      693 CH.sub.2 CH.sub.2 2-oxetanyl                                               694 CH.sub.2 CH.sub.2 3-hydroxy-3-methyl-2-oxetanyl                            695 CH.sub.2 CH.sub.2 3-hydroxy-3-ethyl-2-oxetanyl                             696 CH.sub.2 CH.sub.2 3-hydroxy-3-propyl-2-oxetanyl                            697 CH.sub.2 CH.sub.2 3-hydroxy-3-butyl-2-oxetanyl                             698 CH.sub.2 CH.sub.2 3-methoxy-3-methyl-2-oxetanyl                            699 CH.sub.2 CH.sub.2 3-methoxy-3-ethyl-2-oxetanyl                             700 CH.sub.2 CH.sub.2 3-methoxy-3-propyl-2-oxetanyl                            701 CH.sub.2 CH.sub.2 3-methoxy-3-butyl-2-oxetanyl                             702 CH.sub.2 CH.sub.2 3-trimethylsilyloxy-3-methyl-2-oxetanyl                  703 CH.sub.2 CH.sub.2 3-trimethylsilyloxy-3-ethyl-2-oxetanyl                   704 CH.sub.2 CH.sub.2 3-trimethylsilyloxy-3-propyl-2-oxetanyl                  705 CH.sub.2 CH.sub.2 3-trimethylsilyloxy-3-butyl-2-oxetanyl                   706 CH.sub.2 CH.sub.2 3-oxetanyl                                               707 CH.sub.2 CH.sub.2 2-furyl                                                  708 CH.sub.2 CH.sub.2 4,5-dihydro-2-furyl                                      709 CH.sub.2 CH.sub.2 2,3-dihydro-2-furyl                                      710 CH.sub.2 CH.sub.2 3-furyl                                                  711 CH.sub.2 CH.sub.2 4,5-dihydro-3-furyl                                      712 CH.sub.2 CH.sub.2 2,3-dihydro-3-furyl                                      713 CH.sub.2 CH.sub.2 2-thienyl                                                714 CH.sub.2 CH.sub.2 4,5-dihydro-2-thienyl                                    715 CH.sub.2 CH.sub.2 2,3-dihydro-2-thienyl                                    716 CH.sub.2 CH.sub.2 5-chloro-2-thienyl                                       717 CH.sub.2 CH.sub.2 5-methyl-2-thienyl                                       718 CH.sub.2 CH.sub.2 3-thienyl                                                719 CH.sub.2 CH.sub.2 4,5-dihydro-3-thienyl                                    720 CH.sub.2 CH.sub.2 2,3-dihydro-3-thienyl                                    721 CH.sub.2 CH.sub.2 2-pyrrolyl                                               722 CH.sub.2 CH.sub.2 2,5-dihydro-2-pyrrolyl                                   723 CH.sub.2 CH.sub.2 3-pyrrole                                                724 CH.sub.2 CH.sub.2 2,5-dihydro-3-pyrrolyl                                   725 CH.sub.2 CH.sub.2 3-isoxazolyl                                             726 CH.sub.2 CH.sub.2 4-methyl-3-isoxazolyl                                    727 CH.sub.2 CH.sub.2 5-methyl-3-isoxazolyl                                    728 CH.sub.2 CH.sub.2 4,5-dimethyl-3-isoxazolyl                                729 CH.sub.2 CH.sub.2 4,5-dihydro-3-isoxazolyl                                 730 CH.sub.2 CH.sub.2 4-methyl-4,5-dihydro-3-isoxazolyl                        731 CH.sub.2 CH.sub.2 5-methyl-4,5-dihydro-3-isoxazolyl                        732 CH.sub.2 CH.sub.2 4,5-dimethyl-4,5-dihydro-3-isoxazolyl                    733 CH.sub.2 CH.sub.2 4-isoxazolyl                                             734 CH.sub.2 CH.sub.2 3-methyl-4-isoxazolyl                                    735 CH.sub.2 CH.sub.2 5-methyl-4-isoxazolyl                                    736 CH.sub.2 CH.sub.2 5-cyclopropyl-4-isoxazolyl                               737 CH.sub.2 CH.sub.2 5-phenyl-4-isoxazolyl                                    738 CH.sub.2 CH.sub.2 3,5-dimethyl-4-isoxazolyl                                739 CH.sub.2 CH.sub.2 4,5-dihydro-4-isoxazolyl                                 740 CH.sub.2 CH.sub.2 3-methyl-4,5-dihydro-4-isoxazolyl                        741 CH.sub.2 CH.sub.2 5-methyl-4,5-dihydro-4-isoxazolyl                        742 CH.sub.2 CH.sub.2 3,5-dimethyl-4,5-dihydro-4-isoxazolyl                    743 CH.sub.2 CH.sub.2 5-isoxazolyl                                             744 CH.sub.2 CH.sub.2 3-methyl-5-isoxazolyl                                    745 CH.sub.2 CH.sub.2 4-methyl-5-isoxazolyl                                    746 CH.sub.2 CH.sub.2 3,4-dimethyl-5-isoxazolyl                                747 CH.sub.2 CH.sub.2 4,5-dihydro-5-isoxazolyl                                 748 CH.sub.2 CH.sub.2 3-methyl-4,5-dihydro-5-isoxazolyl                        749 CH.sub.2 CH.sub.2 4-methyl-4,5-dihydro-5-isoxazolyl                        750 CH.sub.2 CH.sub.2 3,4-dimethyl-4,5-dihydro-5-isoxazolyl                    751 CH.sub.2 CH.sub.2 3-isothiazolyl                                           752 CH.sub.2 CH.sub.2 4-methyl-3-isothiazolyl                                  753 CH.sub.2 CH.sub.2 5-methyl-3-isothiazolyl                                  754 CH.sub.2 CH.sub.2 4-isothiazolyl                                           755 CH.sub.2 CH.sub.2 3-methyl-4-isothiazolyl                                  756 CH.sub.2 CH.sub.2 5-methyl-4-isothiazolyl                                  757 CH.sub.2 CH.sub.2 5-isothiazolyl                                           758 CH.sub.2 CH.sub.2 3-methyl-5-isothiazolyl                                  759 CH.sub.2 CH.sub.2 4-methyl-5-isothiazolyl                                  760 CH.sub.2 CH.sub.2 2-oxazolyl                                               761 CH.sub.2 CH.sub.2 4-oxazolyl                                               762 CH.sub.2 CH.sub.2 5-oxazolyl                                               763 CH.sub.2 CH.sub.2 2-thiazolyl                                              764 CH.sub.2 CH.sub.2 4-thiazolyl                                              765 CH.sub.2 CH.sub.2 5-thiazolyl                                              766 CH.sub.2 CH.sub.2 3-pyrazolyl                                              767 CH.sub.2 CH.sub.2 4-pyrazolyl                                              768 CH.sub.2 CH.sub.2 1-methyl-3-pyrazolyl                                     769 CH.sub.2 CH.sub.2 1-methyl-4-pyrazolyl                                     770 CH.sub.2 CH.sub.2 1-methyl-5-pyrazolyl                                     771 CH.sub.2 CH.sub.2 2-imidazolyl                                             772 CH.sub.2 CH.sub.2 1-methyl-2-imidazolyl                                    773 CH.sub.2 CH.sub.2 5-methyl-[1,3,4]-2-oxadiazolyl                           774 CH.sub.2 CH.sub.2 5-methyl-[1,2,4]-3-oxadiazolyl                           775 CH.sub.2 CH.sub.2 5-methyl-[1,3,4]-2-thiadiazolyl                          776 CH.sub.2 CH.sub.2 5-methyl-[1,2,4]-3-thiadiazolyl                          777 CH.sub.2 CH.sub.2 [1,2,4]-3-triazolyl                                      778 CH.sub.2 CH.sub.2 [1,2,3]-4-triazolyl                                      779 CH.sub.2 CH.sub.2 2-pyridyl                                                780 CH.sub.2 CH.sub.2 6-chloro-2-pyridyl                                       781 CH.sub.2 CH.sub.2 6-methoxy-2-pyridyl                                      782 CH.sub.2 CH.sub.2 6-trifluoromethyl-2-pyridyl                              783 CH.sub.2 CH.sub.2 3-pyridyl                                                784 CH.sub.2 CH.sub.2 2-chloro-3-pyridyl                                       785 CH.sub.2 CH.sub.2 2-methoxy-3-pyridyl                                      786 CH.sub.2 CH.sub.2 4-pyridyl                                                787 CH.sub.2 CH.sub.2 2-chloro-4-pyridyl                                       788 CH.sub.2 CH.sub.2 2-methoxy-4-pyridyl                                      789 CH.sub.2 CH.sub.2 2-ethoxy-4-pyridyl                                       790 CH.sub.2 CH.sub.2 2-methylthio-4-pyridyl                                   791 CH.sub.2 CH.sub.2 2-trifluoromethyl-5-pyridyl                              792 CH.sub.2 CH.sub.2 2-pyrimidinyl                                            793 CH.sub.2 CH.sub.2 3-pyrimidinyl                                            794 CH.sub.2 CH.sub.2 4-pyrimidinyl                                            795 CH.sub.2 CH.sub.2 2-pyrazinyl                                              796 CH.sub.2 CH.sub.2 3-pyridazinyl                                            797 CH.sub.2 CH.sub.2 4-pyridazinyl                                            798 CH.sub.2 CH.sub.2 2-(2H-1,3-oxazinyl)                                      799 CH.sub.2 CH.sub.2 2-(6H-1,3-oxazinyl)                                      800 CH.sub.2 CH.sub.2 4-(6H-1,3-oxazinyl)                                      801 CH.sub.2 CH.sub.2 6-(6H-1,3-oxazinyl)                                      802 CH.sub.2 CH.sub.2 [1,3,5]-2-triazinyl                                      803 CH.sub.2 CH.sub.2 [1,2,4]-3-triazinyl                                      804 CH.sub.2 CH.sub.2 [1,2,4]-5-triazinyl                                      805 CH.sub.2 CH.sub.2 [1,2,4]-6-triazinyl                                      806 --C.tbd.C-- oxiranyl                                                       807 --C.tbd.C-- 3-methyl-2-oxiranyl                                            808 --C.tbd.C-- 2-oxetanyl                                                     809 --C.tbd.C-- 3-hydroxy-3-methyl-2-oxetanyl                                  810 --C.tbd.C-- 3-hydroxy-3-ethyl-2-oxetanyl                                   811 --C.tbd.C-- 3-hydroxy-3-propyl-2-oxetanyl                                  812 --C.tbd.C-- 3-hydroxy-3-butyl-2-oxetanyl                                   813 --C.tbd.C-- 3-methoxy-3-methyl-2-oxetanyl                                  814 --C.tbd.C-- 3-methoxy-3-ethyl-2-oxetanyl                                   815 --C.tbd.C-- 3-methoxy-3-propyl-2-oxetanyl                                  816 --C.tbd.C-- 3-methoxy-3-butyl-2-oxetanyl                                   817 --C.tbd.C-- 3-trimethylsilyloxy-3-methyl-2-oxetanyl                        818 --C.tbd.C-- 3-trimethylsilyloxy-3-ethyl-2-oxetanyl                         819 --C.tbd.C-- 3-trimethylsilyloxy-3-propyl-2-oxetanyl                        820 --C.tbd.C-- 3-trimethylsilyloxy-3-butyl-2-oxetanyl                         821 --C.tbd.C-- 3-oxetanyl                                                     822 --C.tbd.C-- 2-furyl                                                        823 --C.tbd.C-- 4,5-dihydro-2-furyl                                            824 --C.tbd.C-- 2,3-dihydro-2-furyl                                            825 --C.tbd.C-- 3-furyl                                                        826 --C.tbd.C-- 4,5-dihydro-3-furyl                                            827 --C.tbd.C-- 2,3-dihydro-3-furyl                                            828 --C.tbd.C-- 2-thienyl                                                      829 --C.tbd.C-- 4,5-dihydro-2-thienyl                                          830 --C.tbd.C-- 2,3-dihydro-2-thienyl                                          831 --C.tbd.C-- 5-chloro-2-thienyl                                             832 --C.tbd.C-- 5-methyl-2-thienyl                                             833 --C.tbd.C-- 3-thienyl                                                      834 --C.tbd.C-- 4,5-dihydro-3-thienyl                                          835 --C.tbd.C-- 2,3-dihydro-3-thienyl                                          836 --C.tbd.C-- 2-pyrrolyl                                                     837 --C.tbd.C-- 2,5-dihydro-2-pyrrolyl                                         838 --C.tbd.C-- 3-pyrrole                                                      839 --C.tbd.C-- 2,5-dihydro-3-pyrrolyl                                         840 --C.tbd.C-- 3-isoxazolyl                                                   841 --C.tbd.C-- 4-methyl-3-isoxazolyl                                          842 --C.tbd.C-- 5-methyl-3-isoxazolyl                                          843 --C.tbd.C-- 4,5-dimethyl-3-isoxazolyl                                      844 --C.tbd.C-- 4,5-dihydro-3-isoxazolyl                                       845 --C.tbd.C-- 4-methyl-4,5-dihydro-3-isoxazolyl                              846 --C.tbd.C-- 5-methyl-4,5-dihydro-3-isoxazolyl                              847 --C.tbd.C-- 4,5-dimethyl-4,5-dihydro-3-isoxazolyl                          848 --C.tbd.C-- 4-isoxazolyl                                                   849 --C.tbd.C-- 3-methyl-4-isoxazolyl                                          850 --C.tbd.C-- 5-methyl-4-isoxazolyl                                          851 --C.tbd.C-- 5-cyclopropyl-4-isoxazolyl                                     852 --C.tbd.C-- 5-phenyl-4-isoxazolyl                                          853 --C.tbd.C-- 3,5-dimethyl-4-isoxazolyl                                      854 --C.tbd.C-- 4,5-dihydro-4-isoxazolyl                                       855 --C.tbd.C-- 3-methyl-4,5-dihydro-4-isoxazolyl                              856 --C.tbd.C-- 5-methyl-4,5-dihydro-4-isoxazolyl                              857 --C.tbd.C-- 3,5-dimethyl-4,5-dihydro-4-isoxazolyl                          858 --C.tbd.C-- 5-isoxazolyl                                                   859 --C.tbd.C-- 3-methyl-5-isoxazolyl                                          860 --C.tbd.C-- 4-methyl-5-isoxazolyl                                          861 --C.tbd.C-- 3,4-dimethyl-5-isoxazolyl                                      862 --C.tbd.C-- 4,5-dihydro-5-isoxazolyl                                       863 --C.tbd.C-- 3-methyl-4,5-dihydro-5-isoxazolyl                              864 --C.tbd.C-- 4-methyl-4,5-dihydro-5-isoxazolyl                              865 --C.tbd.C-- 3,4-dimethyl-4,5-dihydro-5-isoxazolyl                          866 --C.tbd.C-- 3-isothiazolyl                                                 867 --C.tbd.C-- 4-methyl-3-isothiazolyl                                        868 --C.tbd.C-- 5-methyl-3-isothiazolyl                                        869 --C.tbd.C-- 4-isothiazolyl                                                 870 --C.tbd.C-- 3-methyl-4-isothiazolyl                                        871 --C.tbd.C-- 5-methyl-4-isothiazolyl                                        872 --C.tbd.C-- 5-isothiazolyl                                                 873 --C.tbd.C-- 3-methyl-5-isothiazolyl                                        874 --C.tbd.C-- 4-methyl-5-isothiazolyl                                        875 --C.tbd.C-- 2-oxazolyl                                                     876 --C.tbd.C-- 4-oxazolyl                                                     877 --C.tbd.C-- 5-oxazolyl                                                     878 --C.tbd.C-- 2-thiazolyl                                                    879 --C.tbd.C-- 4-thiazolyl                                                    880 --C.tbd.C-- 5-thiazolyl                                                    881 --C.tbd.C-- 3-pyrazolyl                                                    882 --C.tbd.C-- 4-pyrazolyl                                                    883 --C.tbd.C-- 1-methyl-3-pyrazolyl                                           884 --C.tbd.C-- 1-methyl-4-pyrazolyl                                           885 --C.tbd.C-- 1-methyl-5-pyrazolyl                                           886 --C.tbd.C-- 2-imidazolyl                                                   887 --C.tbd.C-- 1-methyl-2-imidazolyl                                          888 --C.tbd.C-- 5-methyl-[1,3,4]-2-oxadiazolyl                                 889 --C.tbd.C-- 5-methyl-[1,2,4]-3-oxadiazolyl                                 890 --C.tbd.C-- 5-methyl-[1,3,4]-2-thiadiazolyl                                891 --C.tbd.C-- 5-methyl-[1,2,4]-3-thiadiazolyl                                892 --C.tbd.C-- [1,2,4]-3-triazolyl                                            893 --C.tbd.C-- [1,2,3]-4-triazolyl                                            894 --C.tbd.C-- 2-pyridyl                                                      895 --C.tbd.C-- 6-chloro-2-pyridyl                                             896 --C.tbd.C-- 6-methoxy-2-pyridyl                                            897 --C.tbd.C-- 6-trifluoromethyl-2-pyridyl                                    898 --C.tbd.C-- 3-pyridyl                                                      899 --C.tbd.C-- 2-chloro-3-pyridyl                                             900 --C.tbd.C-- 2-methoxy-3-pyridyl                                            901 --C.tbd.C-- 4-pyridyl                                                      902 --C.tbd.C-- 2-chloro-4-pyridyl                                             903 --C.tbd.C-- 2-methoxy-4-pyridyl                                            904 --C.tbd.C-- 2-ethoxy-4-pyridyl                                             905 --C.tbd.C-- 2-methylthio-4-pyridyl                                         906 --C.tbd.C-- 2-trifluoromethyl-5-pyridyl                                    907 --C.tbd.C-- 2-pyrimidinyl                                                  908 --C.tbd.C-- 3-pyrimidinyl                                                  909 --C.tbd.C-- 4-pyrimidinyl                                                  910 --C.tbd.C-- 2-pyrazinyl                                                    911 --C.tbd.C-- 3-pyridazinyl                                                  912 --C.tbd.C-- 4-pyridazinyl                                                  913 --C.tbd.C-- 2-(2H-1,3-oxazinyl)                                            914 --C.tbd.C-- 2-(6H-1,3-oxazinyl)                                            915 --C.tbd.C-- 4-(6H-1,3-oxazinyl)                                            916 --C.tbd.C-- 6-(6H-1,3-oxazinyl)                                            917 --C.tbd.C-- [1,3,5]-2-triazinyl                                            918 --C.tbd.C-- [1,2,4]-3-triazinyl                                            919 --C.tbd.C-- [1,2,4]-5-triazinyl                                            920 --C.tbd.C-- [1,2,4]-6-triazinyl                                          ______________________________________                                    

Tables 1-144 below are based on the 4-benzoylpyrazoles of the formula Ib. ##STR15##

Table 1: Compounds 1.1-1.920

Compounds of the formula Ib in which R¹ is chlorine and R² is chlorine, R⁵ is methyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 2: Compounds 2.1-2.920

Compounds of the formula Ib in which R¹ is chlorine and R² is chlorine, R⁵ is ethyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 3: Compounds 3.1-3.920

Compounds of the formula Ib in which R¹ is chlorine and R² is chlorine, R⁵ is n-propyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 4: Compounds 4.1-4.920

Compounds of the formula Ib in which R¹ is chlorine and R² is chlorine, R⁵ is methyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 5: Compounds 5.1-5.920

Compounds of the formula Ib in which R¹ is chlorine and R² is chlorine, R⁵ is ethyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 6: Compounds 6.1-6.920

Compounds of the formula Ib in which R¹ is chlorine and R² is chlorine, R⁵ is n-propyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 7: Compounds 7.1-7.920

Compounds of the formula Ib in which R¹ is chlorine and R² is chlorine, R⁵ is methyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 8: Compounds 8.1-8.920

Compounds of the formula Ib in which R¹ is chlorine and R² is chlorine, R⁵ is ethyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 9: Compounds 9.1-9.920

Compounds of the formula Ib in which R¹ is chlorine and R² is chlorine, R⁵ is n-propyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 10: Compounds 10.1-10.920

Compounds of the formula Ib in which R¹ is chlorine and R² is chlorine, R⁵ is methyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 11: Compounds 11.1-11.920

Compounds of the formula Ib in which R¹ is chlorine and R² is chlorine, R⁵ is ethyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 12: Compounds 12.1-12.920

Compounds of the formula Ib in which R¹ is chlorine and R² is chlorine, R⁵ is n-propyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 13: Compounds 13.1-13.920

Compounds of the formula Ib in which R¹ is chlorine and R² is chlorine, R⁵ is methyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 14: Compounds 14.1-14.920

Compounds of the formula Ib in which R¹ is chlorine and R² is chlorine, R⁵ is ethyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 15: Compounds 15.1-15.920

Compounds of the formula Ib in which R¹ is chlorine and R² is chlorine, R⁵ is n-propyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 16: Compounds 16.1-16.920

Compounds of the formula Ib in which R¹ is chlorine and R² is chlorine, R⁵ is methyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 17: Compounds 17.1-17.920

Compounds of the formula Ib in which R¹ is chlorine and R² is chlorine, R⁵ is ethyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 18: Compounds 18.1-18.920

Compounds of the formula Ib in which R¹ is chlorine and R² is chlorine, R⁵ is n-propyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 19: Compounds 19.1-19.920

Compounds of the formula Ib in which R¹ is chlorine and R² is chlorine, R⁵ is methyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 20: Compounds 20.1-20.920

Compounds of the formula Ib in which R¹ is chlorine and R² is chlorine, R⁵ is ethyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 21: Compounds 21.1-21.920

Compounds of the formula Ib in which R¹ is chlorine and R² is chlorine, R⁵ is n-propyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 22: Compounds 22.1-22.920

Compounds of the formula Ib in which R¹ is chlorine and R² is chlorine, R⁵ is methyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 23: Compounds 23.1-23.920

Compounds of the formula Ib in which R¹ is chlorine and R² is chlorine, R⁵ is ethyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 24: Compounds 24.1-24.920

Compounds of the formula Ib in which R¹ is chlorine and R² is chlorine, R⁵ is n-propyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 25: Compounds 25.1-25.920

Compounds of the formula Ib in which R¹ is chlorine and R² is methylsulfonyl, R⁵ is methyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 26: Compounds 26.1-26.920

Compounds of the formula Ib in which R¹ is chlorine and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 27: Compounds 27.1-27.920

Compounds of the formula Ib in which R¹ is chlorine and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 28: Compounds 28.1-28.920

Compounds of the formula Ib in which R¹ is chlorine and R² is methylsulfonyl, R⁵ is methyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 29: Compounds 29.1-29.920

Compounds of the formula Ib in which R¹ is chlorine and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 30: Compounds 30.1-30.920

Compounds of the formula Ib in which R¹ is chlorine and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 31: Compounds 31.1-31.920

Compounds of the formula Ib in which R¹ is chlorine and R² is methylsulfonyl, R⁵ is methyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 32: Compounds 32.1-32.920

Compounds of the formula Ib in which R¹ is chlorine and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 33: Compounds 33.1-33.920

Compounds of the formula Ib in which R¹ is chlorine and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 34: Compounds 34.1-34.920

Compounds of the formula Ib in which R¹ is chlorine and R² is methylsulfonyl, R⁵ is methyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 35: Compounds 35.1-35.920

Compounds of the formula Ib in which R¹ is chlorine and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 36: Compounds 36.1-36.920

Compounds of the formula Ib in which R¹ is chlorine and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 37: Compounds 37.1-37.920

Compounds of the formula Ib in which R¹ is chlorine and R² is methylsulfonyl, R⁵ is methyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 38: Compounds 38.1-38.920

Compounds of the formula Ib in which R¹ is chlorine and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 39: Compounds 39.1-39.920

Compounds of the formula Ib in which R¹ is chlorine and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 40: Compounds 40.1-40.920

Compounds of the formula Ib in which R¹ is chlorine and R² is methylsulfonyl, R⁵ is methyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 41: Compounds 41.1-41.920

Compounds of the formula Ib in which R¹ is chlorine and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 42: Compounds 42.1-42.920

Compounds of the formula Ib in which R¹ is chlorine and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 43: Compounds 43.1-43.920

Compounds of the formula Ib in which R¹ is chlorine and R² is methylsulfonyl, R⁵ is methyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 44: Compounds 44.1-44.920

Compounds of the formula Ib in which R¹ is chlorine and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 45: Compounds 45.1-45.920

Compounds of the formula Ib in which R¹ is chlorine and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 46: Compounds 46.1-46.920

Compounds of the formula Ib in which R¹ is chlorine and R² is methylsulfonyl, R⁵ is methyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 47: Compounds 47.1-47.920

Compounds of the formula Ib in which R¹ is chlorine and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 48: Compounds 48.1-48.920

Compounds of the formula Ib in which R¹ is chlorine and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 49: Compounds 49.1-49.920

Compounds of the formula Ib in which R¹ is chlorine and R² is trifluoromethyl, R⁵ is methyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 50: Compounds 50.1-50.920

Compounds of the formula Ib in which R¹ is chlorine and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 51: Compounds 51.1-51.920

Compounds of the formula Ib in which R¹ is chlorine and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 52: Compounds 52.1-52.920

Compounds of the formula Ib in which R¹ is chlorine and R² is trifluoromethyl, R⁵ is methyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 53: Compounds 53.1-53.920

Compounds of the formula Ib in which R¹ is chlorine and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 54: Compounds 54.1-54.920

Compounds of the formula Ib in which R¹ is chlorine and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 55: Compounds 55.1-55.920

Compounds of the formula Ib in which R¹ is chlorine and R² is trifluoromethyl, R⁵ is methyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 56: Compounds 56.1-56.920

Compounds of the formula Ib in which R¹ is chlorine and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 57: Compounds 57.1-57.920

Compounds of the formula Ib in which R¹ is chlorine and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 58: Compounds 58.1-58.920

Compounds of the formula Ib in which R¹ is chlorine and R² is trifluoromethyl, R⁵ is methyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 59: Compounds 59.1-59.920

Compounds of the formula Ib in which R¹ is chlorine and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 60: Compounds 60.1-60.920

Compounds of the formula Ib in which R¹ is chlorine and R² is chlorine, R⁵ is n-propyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 61: Compounds 61.1-61.920

Compounds of the formula Ib in which R¹ is chlorine and R² is trifluoromethyl, R⁵ is methyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 62: Compounds 62.1-62.920

Compounds of the formula Ib in which R¹ is chlorine and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 63: Compounds 63.1-63.920

Compounds of the formula Ib in which R¹ is chlorine and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 64: Compounds 64.1-64.920

Compounds of the formula Ib in which R¹ is chlorine and R² is trifluoromethyl, R⁵ is methyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 65: Compounds 65.1-65.920

Compounds of the formula Ib in which R¹ is chlorine and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 66: Compounds 66.1-66.920

Compounds of the formula Ib in which R¹ is chlorine and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 67: Compounds 67.1-67.920

Compounds of the formula Ib in which R¹ is chlorine and R² is trifluoromethyl, R⁵ is methyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 68: Compounds 68.1-68.920

Compounds of the formula Ib in which R¹ is chlorine and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 69: Compounds 69.1-69.920

Compounds of the formula Ib in which R¹ is chlorine and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 70: Compounds 70.1-70.920

Compounds of the formula Ib in which R¹ is chlorine and R² is trifluoromethyl, R⁵ is methyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 71: Compounds 71.1-71.920

Compounds of the formula Ib in which R¹ is chlorine and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 72: Compounds 72.1-72.920

Compounds of the formula Ib in which R¹ is chlorine and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 73: Compounds 73.1-73.920

Compounds of the formula Ib in which R¹ is methyl and R² is chlorine, R⁵ is methyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 74: Compounds 74.1-74.920

Compounds of the formula Ib in which R¹ is methyl and R² is chlorine, R⁵ is ethyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 75: Compounds 75.1-75.920

Compounds of the formula Ib in which R¹ is methyl and R² is chlorine, R⁵ is n-propyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 76: Compounds 76.1-76.920

Compounds of the formula Ib in which R¹ is methyl and R² is chlorine, R⁵ is methyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 77: Compounds 77.1-77.920

Compounds of the formula Ib in which R¹ is methyl and R² is chlorine, R⁵ is ethyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 78: Compounds 78.1-78.920

Compounds of the formula Ib in which R¹ is methyl and R² is chlorine, R⁵ is n-propyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 79: Compounds 79.1-79.920

Compounds of the formula Ib in which R¹ is methyl and R² is chlorine, R⁵ is methyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 80: Compounds 80.1-80.920

Compounds of the formula Ib in which R¹ is methyl and R² is chlorine, R⁵ is ethyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 81: Compounds 81.1-81.920

Compounds of the formula Ib in which R¹ is methyl and R² is chlorine, R⁵ is n-propyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 82: Compounds 82.1-82.920

Compounds of the formula Ib in which R¹ is methyl and R² is chlorine, R⁵ is methyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 83: Compounds 83.1-83.920

Compounds of the formula Ib in which R¹ is methyl and R² is chlorine, R⁵ is ethyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 84: Compounds 84.1-84.920

Compounds of the formula Ib in which R¹ is methyl and R² is chlorine, R⁵ is n-propyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 85: Compounds 85.1-85.920

Compounds of the formula Ib in which R¹ is methyl and R² is chlorine, R⁵ is methyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 86: Compounds 86.1-86.920

Compounds of the formula Ib in which R¹ is methyl and R² is chlorine, R⁵ is ethyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 87: Compounds 87.1-87.920

Compounds of the formula Ib in which R¹ is methyl and R² is chlorine, R⁵ is n-propyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 88: Compounds 88.1-88.920

Compounds of the formula Ib in which R¹ is methyl and R² is chlorine, R⁵ is methyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 89: Compounds 89.1-89.920

Compounds of the formula Ib in which R¹ is methyl and R² is chlorine, R⁵ is ethyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 90: Compounds 90.1-90.920

Compounds of the formula Ib in which R¹ is methyl and R² is chlorine, R⁵ is n-propyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 91: Compounds 91.1-91.920

Compounds of the formula Ib in which R¹ is methyl and R² is chlorine, R⁵ is methyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 92: Compounds 92.1-92.920

Compounds of the formula Ib in which R¹ is methyl and R² is chlorine, R⁵ is ethyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 93: Compounds 93.1-93.920

Compounds of the formula Ib in which R¹ is methyl and R² is chlorine, R⁵ is n-propyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 94: Compounds 94.1-94.920

Compounds of the formula Ib in which R¹ is methyl and R² is chlorine, R⁵ is methyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 95: Compounds 95.1-95.920

Compounds of the formula Ib in which R¹ is methyl and R² is chlorine, R⁵ is ethyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 96: Compounds 96.1-96.920

Compounds of the formula Ib in which R¹ is methyl and R² is chlorine, R⁵ is n-propyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 97: Compounds 97.1-97.920

Compounds of the formula Ib in which R¹ is methyl and R² is methylsulfonyl, R⁵ is methyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 98: Compounds 98.1-98.920

Compounds of the formula Ib in which R¹ is methyl and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 99: Compounds 99.1-99.920

Compounds of the formula Ib in which R¹ is methyl and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 100: Compounds 100.1-100.920

Compounds of the formula Ib in which R¹ is methyl and R² is methylsulfonyl, R⁵ is methyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 101: Compounds 101.1-101.920

Compounds of the formula Ib in which R¹ is methyl and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 102: Compounds 102.1-102.920

Compounds of the formula Ib in which R¹ is methyl and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 103: Compounds 103.1-103.920

Compounds of the formula Ib in which R¹ is methyl and R² is methylsulfonyl, R⁵ is methyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 104: Compounds 104.1-104.920

Compounds of the formula Ib in which R¹ is methyl and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 105: Compounds 105.1-105.920

Compounds of the formula Ib in which R¹ is methyl and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 106: Compounds 106.1-106.920

Compounds of the formula Ib in which R¹ is methyl and R² is methylsulfonyl, R⁵ is methyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 107: Compounds 107.1-107.920

Compounds of the formula Ib in which R¹ is methyl and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 108: Compounds 108.1-108.920

Compounds of the formula Ib in which R¹ is methyl and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 109: Compounds 109.1-109.920

Compounds of the formula Ib in which R¹ is methyl and R² is methylsulfonyl, R⁵ is methyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 110: Compounds 110.1-110.920

Compounds of the formula Ib in which R¹ is methyl and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 111: Compounds 111.1-111.920

Compounds of the formula Ib in which R¹ is methyl and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 112: Compounds 112.1-112.920

Compounds of the formula Ib in which R¹ is methyl and R² is methylsulfonyl, R⁵ is methyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 113: Compounds 113.1-113.920

Compounds of the formula Ib in which R¹ is methyl and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 114: Compounds 114.1-114.920

Compounds of the formula Ib in which R¹ is methyl and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 115: Compounds 115.1-115.920

Compounds of the formula Ib in which R¹ is methyl and R² is methylsulfonyl, R⁵ is methyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 116: Compounds 116.1-116.920

Compounds of the formula Ib in which R¹ is methyl and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 117: Compounds 117.1-117.920

Compounds of the formula Ib in which R¹ is methyl and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 118: Compounds 118.1-118.920

Compounds of the formula Ib in which R¹ is methyl and R² is methylsulfonyl, R⁵ is methyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 119: Compounds 119.1-119.920

Compounds of the formula Ib in which R¹ is methyl and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 120: Compounds 120.1-120.920

Compounds of the formula Ib in which R¹ is methyl and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is 4-methylphenylsulfonyl where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 121: Compounds 121.1-121.920

Compounds of the formula Ib in which R¹ is methyl and R² is trifluoromethyl, R⁵ is methyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 122: Compounds 122.1-122.920

Compounds of the formula Ib in which R¹ is methyl and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 123: Compounds 123.1-123.920

Compounds of the formula Ib in which R¹ is methyl and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 124: Compounds 124.1-124.920

Compounds of the formula Ib in which R¹ is methyl and R² is trifluoromethyl, R⁵ is methyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 125: Compounds 12.1-125.920

Compounds of the formula Ib in which R¹ is methyl and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 126: Compounds 126.1-126.920

Compounds of the formula Ib in which R¹ is methyl and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 127: Compounds 127.1-127.920

Compounds of the formula Ib in which R¹ is methyl and R² is trifluoromethyl, R⁵ is methyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 128: Compounds 128.1-128.920

Compounds of the formula Ib in which R¹ is methyl and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 129: Compounds 129.1-129.920

Compounds of the formula Ib in which R¹ is methyl and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 130: Compounds 130.1-130.920

Compounds of the formula Ib in which R¹ is methyl and R² is trifluoromethyl, R⁵ is methyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 131: Compounds 131.1-131.920

Compounds of the formula Ib in which R¹ is methyl and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 132: Compounds 132.1-132.920

Compounds of the formula Ib in which R¹ is methyl and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 133: Compounds 133.1-133.920

Compounds of the formula Ib in which R¹ is methyl and R² is trifluoromethyl, R⁵ is methyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 134: Compounds 134.1-134.920

Compounds of the formula Ib in which R¹ is methyl and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 135: Compounds 135.1-135.920

Compounds of the formula Ib in which R¹ is methyl and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 136: Compounds 136.1-136.920

Compounds of the formula Ib in which R¹ is methyl and R² is trifluoromethyl, R⁵ is methyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 137: Compounds 137.1-137.920

Compounds of the formula Ib in which R¹ is methyl and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 138: Compounds 138.1-138.920

Compounds of the formula Ib in which R¹ is methyl and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 139: Compounds 139.1-139.920

Compounds of the formula Ib in which R¹ is methyl and R² is trifluoromethyl, R⁵ is methyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 140: Compounds 140.1-140.920

Compounds of the formula Ib in which R¹ is methyl and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 141: Compounds 141.1-141.920

Compounds of the formula Ib in which R¹ is methyl and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 142: Compounds 142.1-142.920

Compounds of the formula Ib in which R¹ is methyl and R² is trifluoromethyl, R⁵ is methyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 143: Compounds 143.1-143.920

Compounds of the formula Ib in which R¹ is methyl and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

Table 144: Compounds 144.1-144.920

Compounds of the formula Ib in which R¹ is methyl and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond in each case to one line of Table A.

The compounds I and their agriculturally useful salts are suitable, both in the form of isomer mixtures and in the form of the pure isomers, as herbicides. The herbicidal compositions comprising I control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and grass weeds in crops such as wheat, rice, maize, soya and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.

Depending on the respective application method, the compounds I, or compositions comprising them, can additionally be employed in a further number of crop plants for eliminating undesirable plants. Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In addition, the compounds I may also be used in crops which tolerate the action of herbicides owing to breeding, including genetic engineering methods.

The herbicidal compositions or the active compounds can be applied pre- or post-emergence. If the active compounds are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that they come into as little contact as possible, if any, with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).

The compounds I, or the compositions comprising them, can be used for example in the form of ready-to-spray aqueous solutions, powders, suspensions, also highly-concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for scattering, or granules, by means of spraying, atomizing, dusting, scattering or watering. The use forms depend on the intended aims; in any case, they should ensure a very fine distribution of the active compounds according to the invention.

Essentiall suitable inert auxiliaries include: mineral oil fractions of medium to high boiling point, such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, e.g. amines such as N-methylpyrrolidone or water.

Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the substituted 4-benzoylpyrazoles, either as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates comprising active compound, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.

Suitable surfactants are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, e.g. ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene, or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin-sulfite waste liquors or methylcellulose.

Powders, materials for scattering and dusts can be prepared by mixing or grinding the active compounds together with a solid carrier.

Granules, e.g. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Solid carriers are mineral earths, such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate and ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.

The concentrations of the active compounds I in the ready-to-use preparations can be varied within wide ranges. In general, the formulations comprise from 0.001 to 98% by weight, preferably 0.01 to 95% by weight of at least one active compound. The active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

The compounds I according to the invention can be formulated for example as follows:

I 20 parts by weight of the compound No. 26.39 are dissolved in a mixture composed of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 to 10 mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonate and 5 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.

II 20 parts by weight of the compound No. 26.39 are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.

III 20 parts by weight of the active compound No. 26.39 are dissolved in a mixture composed of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction of boiling point 210 to 280° C. and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.

IV 20 parts by weight of the active compound No. 26.39 are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalenesulfonate, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives a spray mixture which comprises 0.1% by weight of the active compound.

V 3 parts by weight of the active compound No. 26.39 are mixed with 97 parts by weight of finely divided kaolin. This gives a dust which comprises 3% by weight of active compound.

VI 20 parts by weight of the active compound No. 26.39 are mixed intimately with 2 parts by weight of calcium dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenol/urea/formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. This gives a stable oily dispersion.

VII 1 part by weight of the compound No. 26.39 is dissolved in a mixture composed of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. This gives a stable emulsion concentrate.

VIII 1 part by weight of the compound No. 26.39 is dissolved in a mixture composed of 80 parts by weight of cyclohexane and 20 parts by weight of Wettol® EM 31 (=nonionic emulsifier based on ethoxylated castor oil). This gives a stable emulsion concentrate.

To widen the spectrum of action and to achieve synergistic effects, the substituted 4-benzoylpyrazoles may be mixed with a large number of representatives of other herbicidal or growth-regulating active compound groups and then applied concomitantly. Suitable components for mixtures are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, (het)aryloxyalkanoic acid and its derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-aroyl-1,3-cyclohexanediones, hetaryl aryl ketones, benzylisoxazolidinones, meta-CF₃ -phenyl derivatives, carbamates, quinolinecarboxylic acid and its derivatives, chloroacetanilides, cyclohexane-1,3-dione derivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- or hetaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils.

It may furthermore be advantageous to apply the compounds I, alone or else concomitantly in combination with other herbicides, in the form of a mixture with other crop protection agents, for example together with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are employed for treating nutritional and trace element deficiencies. Nonphytotoxic oils and oil concentrates may also be added.

The rates of application of active compound are from 0.001 to 3.0, preferably 0.01 to 1.0, kg/ha of active substance (a.s.), depending on the control target, the season, the target plants and the growth stage.

The syntheses of some starting materials and products are described below.

2,4-Dichloro-3-((2-pyridyl)(hydroxymethyl)phenyl)(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)methanone

Step a: tert-Butyl 2,4-dichloro-3-((2-pyridyl)(hydroxymethyl))benzoate

At -20° C., 4.0 g (39.6 mmol) of diisopropylamine in 120 ml of tetrahydrofuran are stirred for 40 minutes with 25.0 ml (40.0 mmol) of a 1.6 M n-butyllithium solution in hexane. At -75° C., a solution of 10.0 g (40.5 mmol) of tert-butyl 2,4-dichlorobenzoate in 30 ml of tetrahydrofuran is added dropwise, and the mixture is stirred for 1.5 h. A solution of 4.3 g (40.5 mmol) of 2-formylpyridine in 20 ml of tetrahydropyran is added dropwise and the mixture is stirred at room temperature for 2.5 h. The mixture is poured into 500 ml of saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The combined extracts are washed with water, dried over sodium sulfate, filtered and freed from the solvent under reduced pressure. The crude product is purified by silica gel chromatography using cyclohexane/ethyl acetate. Yield: 7.5 g; ¹ H NMR, δ [ppm], (DMSO-d₆): 1.5 (s), 6.5 (m), 7.2 (m); 7.5 (m), 7.9 (m), 8.4 (d)

Step b: 2,4-Dichloro-3-((2-pyridyl)(hydroxymethyl))benzoic acid

3.5 g (9.9 mmol) of tert-butyl 2,4-dichloro-3-((2-pyridyl)(hydroxymethyl))benzoate in 120 ml of toluene and 60 ml of water together with 1.9 g of p-toluenesulfonic acid are heated under reflux for 9 h. After cooling, the organic phase is separated off and the aqueous phase is admixed with a solution of 23.8 g of sodium dihydrogen phosphate in 280 ml of water and extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate, filtered and freed from the solvent under reduced pressure. Yield: 1.9 g; ¹ H NMR, δ [ppm], (DMSO-d₆): 6.5 (m), 7.2 (m), 7.5 (d), 7.6 (d), 7.95 (m), 8.4 (d), 13.5 (broad s)

Step c: (2,4-Dichloro-3-((2-pyridyl)(hydroxymethyl)phenyl)(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)methanone (Table 2, Example 319; Comp. No. 2.319)

At room temperature, 1.7 g (5.7 mmol) of 2,4-dichloro-3-((2-pyridyl)(hydroxymethyl))benzoic acid, 0.6 g (5.7 mmol) of 1-ethyl-5-hydroxy-1H-pyrazole and 1.2 g (5.7 mmol) of N,N-dicyclohexylcarbodiimide in 25 ml of acetonitrile are stirred for 3 d. The reaction mixture is taken up in 50 ml of 2% strength aqueous sodium hydrogen carbonate solution, filtered and extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate, filtered and freed from the solvent under reduced pressure. The intermediate is dissolved in 10 ml of 1,4-dioxane, admixed with 1.0 g (7.1 mmol) of potassium carbonate and heated under reflux for 8 h. After cooling, the reaction mixture is taken up in 80 ml of water and extracted with methyl tert-butyl ether. The product is precipitated from the aqueous phase by acidification with dilute aqueous hydrochloric acid. ¹ H NMR, δ [ppm], (DMSO-d₆): 1.3 (t), 4.0 (q), 6.6 (s), 7.2 (s), 7.3 (m), 7.4 (d), 7.5 (d), 7.8 (d), 7.9 (m), 8.0 (d)

2,4-Dichloro-3-((2-furyl)(hydroxymethyl)phenyl)(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)methanone

This compound was prepared similarly to the abovementioned procedures. ¹ H NMR, δ [ppm], (DMSO-d₆): 1.3 (t), 3.9 (q), 6.3 (m), 6.4 (broad s); 6.4 (m), 6.5 (m), 7.3 (s), 7.4 (d), 7.6 (m)

Step a: tert-Butyl 2,4-dichloro-3-((2-furyl)(hydroxymethyl))benzoate

At -20° C., 4.0 g (39.6 mmol) of diisopropylamine in 80 ml of tetrahydrofuran are treated for 15 min with 19 ml (30.4 mmol) of 1.6 M n-butyllithium solution in hexane. After cooling to -75° C., a solution of 7.5 g (30.4 mmol) of tert-butyl 2,4-dichlorobenzoate in 20 ml of tetrahydrofuran is added dropwise and the mixture is stirred at room temperature for 12 h. The reaction mixture is admixed with a solution of 2.9 g (30.2 mmol) of 2-formylfuran in 15 ml of tetrahydrofuran and stirred at room temperature for a further 12 h. The mixture is taken up in 300 ml of saturated aqueous sodium chloride solution and extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate, filtered and freed from the solvent under reduced pressure. Yield: 9.2 g; ¹ H-NMR, δ [ppm], (CDCl₃): 1.6 (s), 3.6 (d), 6.2 (m), 6.3 (m), 7.4 (m), 7.7 (d), 7.4 (m), 7.5 (d)

Step b: tert-Butyl 2,4-dichloro-3-((2-furyl)(methoxymethyl))benzoate

At room temperature, 3.0 g (8.8 mmol) of tert-butyl 2,4-dichloro-3-((2-furyl)(hydroxymethyl))benzoate in 40 ml of tetrahydrofuran are stirred for 1 h with 0.4 g (16.6 mmol) of sodium hydride. 6.3 g (43.8 mmol) of iodomethane are added dropwise and the mixture is stirred at room temperature for a further 3 h. The reaction mixture is taken up in 100 ml of saturated aqueous sodium chloride solution, extracted with methyl tert-butyl ether, dried over sodium sulfate, filtered and freed from the solvent under reduced pressure. The crude product is purified by silica gel chromatography using cyclohexane/ethyl acetate. Yield: 2.7 g; ¹ H NMR, δ [ppm], (CDCl₃): 1.6 (s), 3.5 (s), 6.2 (m), 6.3 (m), 7.4 (m), 7.5 (d)

Step c: 2,4-Dichloro-3-((2-furyl)(methoxymethyl))benzoic acid

2.3 g (6.4 mmol) of tert-butyl 2,4-dichloro-3-((2-furyl)(methoxymethyl))benzoate in 50 ml of methanol and 15 ml of water are heated under reflux with 0.7 g (16.1 mmol) of sodium hydroxide for 4 h. 5.0 ml of a 10% strength aqueous sodium hydroxide solution are added and the mixture is heated for a further 3 h. After the reaction mixture has been concentrated under reduced pressure, 50 ml of water are added and the reaction mixture is extracted with dichloromethane. The aqueous phase is acidified using 10% strength aqueous hydrochloric acid and the product is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate, filtered and freed from the solvent under reduced pressure. Yield 1.8 g.

Step d: (2,4-Dichloro-3-((2-furyl)(methoxymethyl)phenyl)(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)methanone (Table 2, Example 362; Comp. No. 2.362)

1.4 g (4.7 mmol) of 2,4-dichloro-3-((2-furyl)(methoxymethyl))benzoic acid, 0.5 g (4.7 mmol) of 1-ethyl-5-hydroxy-1H-pyrazole and 1.0 g (4.7 mmol) of N,N-dicyclohexylcarbodiimide in 10 ml of acetonitrile are stirred at room temperature for 24 h. The reaction mixture is stirred into a 2% strength aqueous sodium hydrogen carbonate solution, extracted with ethyl acetate, dried over sodium sulfate, filtered and freed from the solvent under reduced pressure. The intermediate is purified by silica gel chromatography using ethyl acetate/cyclohexane (Yield: 0.5 g), dissolved in 3 ml of 1,4-dioxane, admixed with 0.2 g (1.2 mmol) of potassium carbonate and heated under reflux for 4 h. The reaction mixture is concentrated under reduced pressure, taken up in 40 ml of water and extracted with methylene chloride. The product is precipitated by acidification of the aqueous phase using 10% strength aqueous hydrochloric acid. Yield: 190 mg; mp. 92 to 93° C.

(2,4-Dichloro-3-((3-furyl)(hydroxymethyl)phenyl)(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)methanone (Table 2, Example 250; Comp. No. 2.250)

This compound is prepared similarly to the abovementioned procedures. ¹ H NMR, δ [ppm], (DMSO-d₆): 1.3 (t), 3.9 (q), 6.1 (broad s), 6.4 (s), 6.5 (s), 7.3 (broad s.), 7.4 (d), 7.5 (s), 7.5 (d), 7.6 (s)

(2,4-Dichloro-3-((3-furyl)(methoxymethyl)phenyl)(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)methanone (Table 2, Example 365; Comp. No. 2.365)

This compound is prepared similarly to the abovementioned procedures. ¹ H NMR, δ [ppm], (DMSO-d₆): 1.3 (t), 3.3 (s), 3.9 (q), 6.1 (s), 6.4 (s), 7.3 (broad s), 7.4 (d), 7.5 (s), 7.6 (d), 7.6 (s)

2,4-Dichloro-3-(3-(5H-furanone)methyl)phenyl)-(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)methanone

Step a: 2,4-Dichloro-3-(3-(5H-furanone)methyl)benzoic acid

The solution of 13 g (0.038 mol) of tert-butyl 2,4-dichloro-3-(3-furyl)hydroxymethylbenzoate (similar to Ex. 2.362 step a) and 1.8 g of p-toluenesulfonic acid in 370 ml of toluene are refluxed for 6 h. The mixture is subsequently poured into 100 ml of 10% strength aqueous sodium hydroxide solution and extracted with ethyl acetate. The aqueous phase is acidified using hydrochloric acid and extracted repeatedly with ethyl acetate. The combined organic phases are washed with water, dried and concentrated. This gives 4.8 g (45%) of the title compound, mp. 196° C.

Step b: 2,4-Dichloro-3-(3-(5H-furanone)methyl)phenyl)-(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)methanone ##STR16##

1.1 g (0.0035 mol) of 2,4-dichloro-3-(3-(5H-furanone)methyl)benzoic acid, 0.4 g (0.0035 mol) of 1-ethyl-5-hydroxy-1H-pyrazole and 0.72 g (0.0035 mol) of dicyclohexylcarbodiimide are stirred in 15 ml of acetonitrile at room temperature for 12 h. The reaction mixture is poured into 100 ml of 2% strength aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic phase is dried and concentrated.

1 g of the residue obtained in this manner and 0.5 g (0.0034 mol) of potassium carbonate in 5 ml of dioxane are refluxed for 5 h. After cooling, the mixture is diluted with 60 ml of water and extracted successively with methylene chloride and methyl tert-butyl ether. The aqueous phase is separated off and acidified with HCl, and the precipitate is filtered off with suction (23%; mp. 90-93° C.).

                  TABLE 145                                                        ______________________________________                                           #STR17##                                                                        -                                      .sup.1 H NMR                           No. R.sup.5 R.sup.6 Het mp. [° C] [ppm]                               ______________________________________                                         145.1                                                                               CH.sub.3                                                                              H        5-methyl-4,5-di-                                                                           90                                                 hydro-3-isoxazolyl                                                          145.2 CH.sub.3 H 5-chloromethyl-4,5-                                              dihydro-3-isoxazolyl 93                                                     145.3 CH.sub.3 iso- 5-chloromethyl-4,5-                                          propyl dihydro-3-isoxazolyl 72                                               145.4 CH.sub.3 SO.sub.2 CH.sub.3 5-chloromethyl-4,5- 87                           dihydro-3-isoxazolyl                                                        145.5 C.sub.2 H.sub.5 H 4,5-dihydro-3- 136                                        isoxazolyl                                                                  145.6 C.sub.2 H.sub.5 H 5-methyl-4,5-dihydro- 92                                  3-isoxazolyl                                                                145.7 C.sub.2 H.sub.5 iso- 5-methyl-4,5-dihydro- 66                              propyl 3-isoxazolyl                                                        ______________________________________                                    

Use Examples

The herbicidal activity of the substituted 4-benzoylpyrazoles of the formula I was demonstrated by the following greenhouse experiments:

The culture containers used were plastic pots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.

For the pre-emergence treatment, the active compounds, which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with translucent plastic hoods until the plants had rooted. This cover causes uniform germination of the test plants, as long as this was not adversely affected by the active compounds.

For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active compounds which had been suspended or emulsified in water. The test plants were for this purpose either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment. The rate of application for the post-emergence treatment was 0.5 or 0.25 kg/ha of a.s.

Depending on the species, the plants were kept at 10-25° C. or 20-35° C. The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the aerial parts, and 0 means no damage, or normal course of growth.

The plants used in the greenhouse experiments belong to the following species:

    ______________________________________                                         Scientific name      Common name                                               ______________________________________                                         Chenopodium album    lambsquarters                                                (goosefoot)                                                                   Echinochloa crus-galli barnyardgrass                                           Setaria faberii giant foxtail                                                  Setaria viridis green foxtail                                                  Zea mays corn                                                                ______________________________________                                    

Selective herbicidal activity when applied post-emergence in the greenhouse ##STR18##

The compound No. 145.5, applied post-emergence, controlled the abovementioned weeds very efficiently at application rates of 0.5 or 0.25 kg/ha of a.s. 

What is claimed is:
 1. A 4-benzoylpyrazole of the formula I ##STR19## where: R¹ and R² are each hydrogen, mercapto, nitro, halogen, cyano, thiocyanato, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy, C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, --OR³, --OCOR³, --OSO₂ R³, --S(O)_(n) R³, --SO₂ OR³, --SO₂ N(R³)₂, --NR³ SO₂ R³ or --NR³ COR³ ;R³ is hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, phenyl or phenyl-C₁ -C₆ -alkyl; where the alkyl radicals mentioned may be partially or fully halogenated and/or carry one to three of the following groups: hydroxyl, mercapto, amino, cyano, R³, --OR³, --SR³, --N(R³)₂, ═NOR³, --OCOR³, --SCOR³, --NR³ COR³, --CO₂ R³, --COSR³, --CON(R³)₂, C₁ -C₄ -alkyliminooxy, C₁ -C₄ -alkoxyamino, C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkoxy-C₂ -C₆ -alkoxycarbonyl, C₁ -C₄ -alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the eight last-mentioned radicals may in turn be substituted; n is 0, 1 or 2; Q is a pyrazole of the formula II which is attached in position 4, ##STR20## where R⁴ is hydrogen, C₁ -C₆ -alkyl or C₁ -C₆ -haloalkyl; R⁵ is C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, phenyl or phenyl which may be partially or fully halogenated and/or carry one to three of the following radicals:nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy; R⁶ is hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkylcarbonyl, C₁ -C₆ -haloalkylcarbonyl, C₁ -C₆ -alkoxycarbonyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆ -haloalkylsulfonyl, phenylcarbonyl, phenylcarbonylmethyl, phenoxycarbonyl or phenylsulfonyl, where the four last-mentioned substituents are either unsubstituted, or the phenyl ring may in each case be partially or fully halogenated and/or carry one to three of the following radicals:nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy; X¹ is a straight-chain or branched C₁ -C₆ -alkylene, a C₂ -C₆ -alkenylene or a C₂ -C₆ -alkynylene chain, where the alkylene, alkenylene or alkynylene radicals mentioned may be partially halogenated and/or carry one to three of the following groups:--OR⁷, --OCOR⁷, --OCONHR⁷ or --OSO₂ R⁷, and where those of the alkenylene radicals mentioned are excluded where the double bond is α,β to the phenyl ring and where Het is linked to the double bond via the β position; R⁷ is hydrogen, C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, phenyl, phenyl-C₁ -C₆ -alkyl, where the alkyl, alkenyl or alkynyl radicals mentioned may be partially or fully halogenated and/or substituted by one or more of the following radicals:hydroxyl, mercapto, amino, cyano, nitro, formyl, C₁ -C₄ -alkylamino, C₁ -C₄ -dialkylamino, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkylcarbonyloxy, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy; Het is a three- to six-membered, partially or fully saturated heterocyclic group or a three- to six-membered heteroaromatic group having up to three hetero atoms selected from the group consisting of:nitrogen, oxygen and sulfur, where the heterocyclic or heteroaromatic group mentioned may be partially or fully halogenated and/or substituted by R⁸ ; and when Het is a piperidinyl radical it is 2-piperidinyl, 3-piperidinyl or 4-piperidinyl; R⁸ is hydrogen, hydroxyl, mercapto, amino, cyano, nitro, formyl, C₁ -C₄ -alkylamino, C₁ -C₄ -dialkylamino, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkylcarbonyloxy, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, where in all instances each of the alkyl radicals may be substituted by one or more of the following radicals:cyano, formyl, C₁ -C₄ -alkylamino, C₁ -C₄ -dialkylamino, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkylcarbonyloxy, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy;and agriculturally useful salts thereof.
 2. A 4-benzoylpyrazole of the formula I as claimed in claim 1, in whichR¹ is nitro, halogen, cyano, thiocyanato, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, --OR³ or --S(O)_(n) R³ ; R² is hydrogen or one of the radicals mentioned above under R¹.
 3. A 4-benzoylpyrazole of the formula Ia as claimed in claim 1, ##STR21## where the substituents R¹, R², Q, X¹ and Het are each as defined under claim
 1. 4. A 4-benzoylpyrazole of the formula Ia as claimed in claim 3 in which X¹ is a C₁ -C₂ -alkylene or C₂ -alkynylene chain.
 5. A 4-benzoylpyrazole of the formula Ia as claimed in claim 1 in which Het is a five- or six-membered, partially or fully saturated heterocyclic or a five- or six-membered heteroaromatic group having up to three hetero atoms selected from the group consisting ofnitrogen, oxygen and sulfur.
 6. A process for preparing 4-benzoylpyrazoles of the formula I as claimed in claim 1, which comprises acylating a pyrazole of the formula Ia in which the substituents R⁵ and R⁴ are each as defined under claim 1 ##STR22## with an activated carboxylic acid IIIa or with a carboxylic acid IIIb, ##STR23## where the substituents R¹, R², X¹ and Het are each as defined in claim 1 and L¹ is a nucleophilically replaceable leaving group, and rearranging the acylation product, if appropriate in the presence of a catalyst, to the compounds I and, if desired, reacting it with a compound of the formula IV,

    L.sup.2 --R.sup.6                                          IV

(where R⁶ ≠H) in which R⁶ is as defined in claim 1, except for hydrogen, and L² is a nucleophilically replaceable leaving group, for preparing 4-benzoylpyrazoles of the formula I where R⁶ ≠H.
 7. A composition comprising a herbicidally effective amount of at least one 4-benzoylpyrazole of the formula I or an agriculturally useful salt of I as claimed in claim 1 and auxiliaries customary for the formulation of crop protection agents.
 8. A process for preparing herbicidally effective compositions as claimed in claim 7, which comprises mixing a herbicidally effective amount of at least one 4-benzoylpyrazole of the formula I or an agriculturally useful salt of I and auxiliaries customary for the formulation of crop protection agents.
 9. A process for controlling undesirable vegetation, which comprises allowing a herbicidally effective amount of at least one 4-benzoylpyrazole of the formula I or an agriculturally useful salt of I as claimed in claim 1 to act on plants, their habitat and/or on seeds. 